403:
113:
137:
459:
72:
280:
3271:
531:
593:
91:
Through a variety of mechanisms, the removal of a hydride equivalent converts a primary or secondary alcohol to an aldehyde or ketone, respectively. The oxidation of primary alcohols to carboxylic acids normally proceeds via the corresponding aldehyde, which is transformed via an
1001:
Song, Z.J.; Zhao, M.; Desmond, R.; Devine, P.; Tschaen, D.M.; Tillyer, R.; Frey, L.; Heid, R.; Xu, F.; Foster, B.; Li, J.; Reamer, R.; Volante, R.; Grabowski, E.J.J.; Dolling, U.H.; Reider, P.J. (1999). "Practical
Asymmetric Synthesis of an Endothelin Receptor Antagonist".
499:
to a solution or suspension of the alcohol in an alkaline aqueous solution. For the reaction to proceed efficiently, the alcohol must be at least partially dissolved in the aqueous solution. This can be facilitated by the addition of an organic co-solvent such as
605:
As a lot of the aforementioned conditions for the oxidations of primary alcohols to acids are harsh and not compatible with common protection groups, organic chemists often use a two-step procedure for the oxidation to acids. The alcohol is oxidized to an
635:
is effected with TEMPO and hypochlorite, then chlorite is added to complete the oxidation. Only primary alcohol oxidation is observed. In conjunction with
Sharpless dihydroxylation, this method can be used to generate enantiopure α-hydroxy acids.
104:) by reaction with water. Thus, the oxidation of a primary alcohol at the aldehyde level without further oxidation to the carboxylic acid is possible by performing the reaction in absence of water, so that no aldehyde hydrate can be formed.
79:
In principle, a simple way to oxidize an alcohols uses an oxygen atom and produce water: In practice, oxygen atoms are unavailable, so the above equation is only conceptual. Instead, most oxidations use oxides-based reagents, such as
1132:
Song, Z. J.; Zhao, M.; Desmond, R.; Devine, P.; Tschaen, D. M.; Tillyer, R.; Frey, L.; Heid, R.; Xu, F.; Foster, B.; Li, J.; Reamer, R.; Volante, R.; Grabowski, E. J. J.; Dolling, U. H.; Reider, P. J.; Okada, S.; Kato, Y.; Mano, E.
180:
but in dichloromethane. The
Ratcliffe variant of Collins reagent relates to details of the preparation of this solution, i.e., the addition of chromium trioxide to a solution of pyridine in methylene
6460:
1243:
249:. The reaction takes between half an hour and two hours to complete. The product is then separated from the spent periodinane. Many iodosyl-based oxidants have been developed, e.g.
5576:
5521:
495:) oxidizes primary alcohols to carboxylic acids very efficiently. This reaction, which was first described in detail by Fournier, is typically carried out by adding KMnO
6289:
5631:
5781:
4415:
245:
is a mild oxidant for the conversion of alcohols to aldehydes or ketones. The reaction is performed under standard conditions, at room temperature, most often in
6510:
940:
Ciufolini, M.A.; Swaminathan, S. (1989). "Synthesis of a model depsipeptide segment of
Luzopeptins (BBM 928), potent antitumor and antiretroviral antibiotics".
6284:
5386:
4110:
65:. The reaction mainly applies to primary and secondary alcohols. Secondary alcohols form ketones, while primary alcohols form aldehydes or carboxylic acids.
5156:
3307:
388:(or household bleach) in acetone has been reported for efficient conversion of secondary alcohols in the presence of primary alcohols (Stevens oxidation).
5956:
3900:
527:, such as secondary alcohols, 1,2-diols, aldehydes, alkenes, oximes, sulfides and thiols, and carbon-carbon double bonds. Thus, selectivity is an issue.
6051:
4155:
6031:
5526:
4693:
1153:
Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K. S.; Kwong, H. L.; Morikawa, K.; Wang, Z. M.; Xu, D.; Zhang, X. L.
4574:
4130:
6121:
371:
5876:
3343:
4708:
6354:
5811:
765:
J. S. Yadav, et al. "Recyclable 2nd generation ionic liquids as green solvents for the oxidation of alcohols with hypervalent iodine reagents",
6304:
5916:
5896:
5856:
4663:
6450:
6375:
6259:
4871:
4275:
3606:
6445:
6274:
5931:
5786:
5416:
6609:
5261:
4498:
5621:
5111:
4786:
6525:
6309:
5331:
5886:
6520:
6234:
6096:
5851:
1219:
6410:
5881:
5796:
5766:
5746:
5611:
5606:
4981:
4906:
4549:
4503:
4370:
3631:
3222:
610:
using one of the many procedures above. This sequence is often used in natural product synthesis as in their synthesis of platencin.
6349:
3022:
1117:
985:
701:
672:
6515:
6475:
6425:
5901:
5651:
5581:
4070:
577:. Problems are the toxicity and environmental unfriendliness of the reagent. Catalytic variant, involving treatment with excess of
6111:
5716:
4609:
4330:
6604:
6101:
3641:
351:
329:
6269:
6026:
5976:
4766:
4698:
4589:
4165:
3920:
3845:
3626:
787:
Stevens R, Chapman KT, Weller HN (1980). "Convenient and inexpensive procedure for oxidation of secondary alcohols to ketones".
5981:
5791:
5266:
5176:
3300:
3251:
378:
6555:
6339:
6279:
5681:
5656:
5566:
5146:
5026:
4060:
3556:
6440:
5926:
5721:
3990:
631:
gives carboxylic acids without chlorination side products. The reaction is usually carried out in two steps in the same pot:
538:
in aqueous NaOH during the obtention of a rare amino acid derivative needed for the preparation of antibiotics isolated from
6545:
6131:
5641:
5151:
5096:
4941:
4901:
4733:
4488:
4205:
4055:
1110:
Oxidation of
Primary Alcohols to Carboxylic Acids: A Guide to Current Common Practice (Basic Reactions in Organic Synthesis)
6505:
6066:
6021:
5511:
5366:
3117:
2211:
2154:
6540:
6455:
6314:
6229:
6126:
5201:
4856:
4524:
3935:
3496:
6430:
6405:
6390:
6086:
5951:
5906:
5671:
5216:
5066:
4280:
3960:
3905:
6435:
6380:
5911:
5326:
5041:
5036:
4529:
4345:
4335:
4050:
3910:
3860:
3855:
3830:
3736:
242:
218:
These salts are less reactive, more easily handled, and more selective than
Collins reagent in oxidations of alcohols.
6490:
6091:
6011:
5626:
5591:
5436:
4861:
4821:
4718:
4493:
4245:
4190:
3790:
3501:
3491:
3466:
1517:
1389:
477:
by four. The direct oxidation of primary alcohols to carboxylic acids can be carried out using a variety of reagents.
6465:
6166:
5971:
5406:
4971:
4946:
4886:
4478:
4185:
3835:
4020:
5756:
5291:
4743:
3965:
3930:
3526:
3461:
3293:
3227:
2526:
1457:
1452:
347:
143:
Chromium(VI) reagents are commonly used for these oxidations. One family of Cr(VI) reagents employs the complex CrO
6324:
5946:
5006:
4931:
4455:
4290:
3975:
3751:
3711:
3456:
717:
J. C. Collins, W.W. Hess (1972). "Aldehydes from
Primary Alcohols by Oxidation with Chromium Trioxide: Heptanal".
6619:
6614:
6565:
6470:
6204:
6176:
6146:
6061:
5991:
5921:
5841:
5741:
5701:
5396:
5016:
4315:
4310:
3772:
3636:
3246:
3237:
3217:
1447:
211:
17:
6530:
6400:
6264:
6106:
5966:
5486:
4460:
4010:
3970:
3721:
166:
in pyridine. It was popularized for selective oxidation of primary and secondary alcohols to carbonyl compounds.
6420:
6016:
5986:
5861:
5816:
5646:
5556:
5371:
5361:
5191:
4748:
4688:
4653:
4440:
4400:
4175:
4045:
3561:
3551:
3481:
2571:
402:
5996:
4976:
4000:
3546:
3426:
112:
6209:
902:
Fournier, H.M. (1907). "Transformation des alcools primaires saturès en acides monobasiques correspondants".
855:"An expedient procedure for the oxidative cleavage of olefinic bonds with PhI(OAc)2, NMO, and catalytic OsO4"
6500:
6359:
6151:
6076:
6056:
5776:
5726:
5586:
5551:
5491:
5421:
4723:
4703:
4435:
4355:
4250:
4210:
4180:
4115:
3985:
3895:
3885:
3761:
3471:
3102:
2468:
6239:
5961:
5711:
5691:
5666:
5616:
5531:
5506:
5461:
5431:
5411:
5381:
5346:
5301:
5276:
5251:
5136:
5061:
4841:
4534:
4470:
4270:
3995:
3915:
3601:
3576:
3353:
3348:
3107:
1934:
1924:
1919:
1492:
1442:
1437:
1212:
488:
427:
6575:
5321:
3945:
2633:
2176:
1944:
1939:
1929:
1862:
1852:
1846:
6161:
6116:
5831:
5801:
5771:
5706:
5686:
5601:
5596:
5561:
5516:
5501:
5496:
5476:
5466:
5401:
5391:
5271:
4791:
4594:
4170:
4125:
3955:
3691:
3411:
3373:
3142:
2531:
2191:
2181:
1914:
1904:
1872:
1867:
1857:
391:
205:
3621:
3616:
2618:
2069:
1909:
1841:
1830:
6214:
6344:
6294:
6244:
6224:
6071:
6046:
5761:
5751:
5636:
5451:
5446:
5376:
5161:
4961:
4921:
4851:
4816:
4771:
4738:
4604:
4579:
4559:
4380:
4340:
4300:
4265:
4195:
3950:
3820:
3795:
3333:
3232:
1899:
1529:
1502:
925:
357:
250:
2872:
2613:
1775:
815:
128:
alcohols represent special cases. Aldehydes are susceptible to over oxidation to carboxylic acids.
6560:
6550:
6535:
6181:
6156:
6141:
6136:
5866:
5821:
5806:
5696:
5676:
5571:
5456:
5441:
5286:
5231:
5221:
5211:
5186:
4951:
4826:
4801:
4713:
4569:
4554:
4539:
4395:
4360:
4305:
4075:
3925:
3870:
3741:
3656:
3516:
3441:
3256:
2608:
2551:
2513:
2186:
2171:
2149:
1497:
1409:
1309:
1228:
618:
411:
385:
323:
75:
Stages in the oxidation of primary alcohols to carboxylic acids via aldehydes and aldehyde hydrates
42:
3586:
2877:
2867:
1764:
136:
6299:
6249:
6219:
6081:
5871:
5661:
5546:
5481:
5471:
5236:
5166:
5131:
5126:
5106:
5101:
5046:
4956:
4806:
4668:
4658:
4564:
4350:
4295:
4225:
4145:
4040:
3940:
3875:
3800:
3646:
3511:
3446:
3170:
3151:
3027:
2643:
2488:
2483:
2478:
2473:
2228:
2094:
1560:
1399:
1291:
1258:
573:, oxidizes alcohols to a carboxylic acid. The protocol frequently affords substantial amounts of
3431:
370:
6036:
5356:
5241:
5206:
5171:
5116:
5071:
5031:
4986:
4966:
4916:
4911:
4881:
4776:
4683:
4619:
4584:
4410:
4285:
4160:
4085:
4065:
3980:
3815:
3810:
3756:
3666:
3571:
3531:
3486:
3368:
3363:
3328:
3274:
3126:
2638:
2241:
2220:
2196:
2144:
2139:
2042:
2022:
2012:
2002:
1997:
1482:
1414:
1350:
1283:
1278:
1205:
1113:
1062:
1036:
981:
942:
884:
835:
745:
697:
668:
640:
632:
562:
524:
435:
269:
226:
81:
71:
38:
1174:
Bal B.S.; Childers, Jr. W.E.; Pinnick H.W. (1981). "Oxidation of α,β-unsaturated aldehydes".
920:
6570:
6415:
6385:
6329:
6254:
6186:
5941:
5891:
5736:
5541:
5316:
5311:
5256:
5246:
5021:
4831:
4811:
4781:
4678:
4614:
4599:
4430:
4385:
4375:
4365:
4260:
4240:
4235:
4220:
4215:
4095:
4090:
4030:
4015:
4005:
3850:
3840:
3706:
3696:
3686:
3596:
3591:
3566:
3506:
3358:
3317:
2675:
2623:
2566:
2393:
2340:
2236:
2134:
2037:
2007:
1987:
1977:
1835:
1487:
1183:
1090:
1052:
1044:
1012:
973:
950:
904:
874:
866:
827:
796:
726:
689:
419:
364:
361:
287:
155:
458:
367:
on Celite. This reagent operates through single electron oxidation by the silver cations.
6480:
6171:
6006:
6001:
5296:
5281:
5226:
5181:
5141:
5091:
5056:
5051:
4996:
4991:
4926:
4876:
4796:
4624:
4508:
4483:
4445:
4420:
4405:
4390:
4325:
4200:
4150:
4140:
4120:
4080:
3890:
3880:
3865:
3661:
3581:
3406:
3401:
3210:
3179:
3112:
3079:
3032:
3017:
2685:
2379:
2374:
2335:
2059:
2027:
1992:
1542:
1477:
1472:
1467:
1462:
1404:
1369:
1268:
644:
552:
474:
470:
466:
447:
295:
265:
261:
246:
169:
62:
54:
3451:
3421:
394:
catalyze the oxidation of alcohols by presence of dioxygen or another terminal oxidant.
6485:
6395:
6334:
5426:
5336:
5306:
5081:
4936:
4673:
4450:
4320:
4135:
4105:
3805:
3701:
3476:
3338:
3241:
3156:
3012:
2561:
2521:
2206:
1982:
1972:
1967:
1957:
1824:
1786:
1769:
1753:
1709:
1698:
1692:
1537:
1432:
1322:
1057:
1031:
879:
854:
299:
279:
120:
Many reagents oxidize secondary alcohols to ketones and primary alcohols to aldehydes.
1187:
954:
480:
Aldehydes are readily oxidized using Cr(VI) and Mn(VII) reagents to carboxylic acids.
6598:
6495:
6196:
6041:
5936:
5731:
5121:
5086:
5076:
5011:
5001:
4891:
4728:
4544:
4255:
4230:
4100:
3746:
3731:
3716:
3611:
3541:
3521:
3436:
3195:
3094:
2653:
2628:
2600:
2543:
2366:
2314:
2201:
2129:
2124:
1962:
1797:
1791:
1780:
1720:
1714:
1703:
1394:
1342:
1317:
1004:
627:
The use of chlorites as terminal oxidants in conjunction with both hypochlorites and
578:
570:
558:
542:, a microorganism found in a soil sample collected in Luzon island in the Philippines
343:
273:
230:
222:
1080:
Nicolaou K.C.; Scott Tria G.; Edmonds D. J. (2008). "Total
Synthesis of Platencin".
530:
5536:
4896:
4648:
4425:
4025:
3825:
3676:
3671:
3536:
3391:
3084:
2460:
2119:
1687:
1512:
1082:
513:
592:
534:
Ciufolini and
Swaminathan oxidized a primary alcohol to carboxylic acid with KMnO
4035:
3681:
3651:
3416:
3200:
3064:
2911:
2503:
2498:
2493:
2284:
1758:
1681:
1675:
418:— suffer oxidative breakage at a carbon-carbon bond with some oxidants such as
6319:
5846:
5196:
3285:
3161:
3146:
3074:
3069:
2974:
2775:
2705:
2581:
2403:
2304:
2114:
2109:
2079:
2074:
2032:
1747:
1630:
1620:
1610:
1565:
1299:
1273:
1253:
190:
839:
730:
2969:
2959:
2941:
2795:
2586:
2441:
2294:
2104:
2099:
2089:
2084:
2064:
1669:
1641:
1635:
1625:
1615:
1570:
977:
693:
85:
1094:
1066:
888:
621:
is an aggressive, seldom-used agent that allows mild reaction conditions.
3726:
3396:
3048:
2964:
2936:
2921:
2916:
2857:
2852:
2836:
2765:
2755:
2725:
2715:
2695:
2431:
2427:
2407:
2389:
2356:
2264:
1600:
1381:
1355:
607:
505:
443:
306:) and – when triethylamine is used as base – triethylammonium chloride (C
46:
800:
3386:
3165:
2926:
2906:
2862:
2818:
2745:
2735:
2576:
2556:
2417:
2274:
1605:
1552:
1507:
1424:
1330:
1263:
831:
816:"Transition metal based catalysts in the aerobic oxidation of alcohols"
509:
501:
1048:
1016:
870:
328:
135:
3174:
2992:
2785:
2017:
125:
50:
2931:
628:
591:
574:
529:
401:
121:
111:
70:
58:
34:
415:
414:
groups located on adjacent carbons —that is, vicinal diols/ 1,2-
3770:
3289:
1201:
601:
Two-step oxidation of alcohols to acids via isolated aldehydes
335:
This seldom-used method interconverts alcohols and carbonyls.
972:. Basic Reactions in Organic Synthesis. 2006. pp. 1–95.
688:. Basic Reactions in Organic Synthesis. 2006. pp. 1–95.
457:
369:
327:
278:
1197:
921:"Sur la préparation des acides gras et de leurs anhydres"
221:
The above reagents represent improvements over the older
814:
Parmeggiani, Camilla; Cardona, Francesca (2012-01-03).
406:
Oxidative cleavage of carbon-carbon bond in 1,2-diols
6461:
Erlenmeyer–Plöchl azlactone and amino-acid synthesis
68:
The reaction can occur using a variety of oxidants.
6368:
6195:
5830:
5345:
4840:
4757:
4637:
4517:
4469:
3779:
3188:
3135:
3093:
3057:
3041:
3005:
2983:
2950:
2897:
2890:
2845:
2827:
2809:
2661:
2652:
2595:
2540:
2512:
2459:
2365:
2349:
2328:
2257:
2250:
2162:
2051:
1881:
1806:
1729:
1651:
1582:
1551:
1423:
1380:
1368:
1341:
1308:
1242:
1235:
1032:"Enantioselective Total Synthesis of Bistramide A"
5522:Divinylcyclopropane-cycloheptadiene rearrangement
454:Oxidation of primary alcohols to carboxylic acids
18:Oxidation of primary alcohols to carboxylic acids
5782:Thermal rearrangement of aromatic hydrocarbons
4416:Thermal rearrangement of aromatic hydrocarbons
970:Oxidation of Alcohols to Aldehydes and Ketones
853:Nicolaou KC, Adsool VA, Hale CR (April 2010).
686:Oxidation of Alcohols to Aldehydes and Ketones
665:Salters Advanced Chemistry: Chemical (2nd ed.)
116:Oxidation of alcohols to aldehydes and ketones
6511:Lectka enantioselective beta-lactam synthesis
3301:
1213:
1030:Crimmins, M.T. & DeBaillie, A.C. (2006).
8:
6290:Inverse electron-demand Diels–Alder reaction
4111:Heterogeneous metal catalyzed cross-coupling
5632:Lobry de Bruyn–Van Ekenstein transformation
208:(PDC) is the pyridium salt of dichromate, .
6192:
4466:
3767:
3308:
3294:
3286:
2894:
2658:
2254:
1377:
1239:
1220:
1206:
1198:
6122:Petrenko-Kritschenko piperidone synthesis
5577:Fritsch–Buttenberg–Wiechell rearrangement
1056:
878:
473:, the terminal carbon atom increases its
6285:Intramolecular Diels–Alder cycloaddition
1108:Marcos Fernández; Gabriel Tojo (2006).
656:
185:A second family of Cr(VI) reagents are
6305:Metal-centered cycloaddition reactions
5957:Debus–Radziszewski imidazole synthesis
3901:Bodroux–Chichibabin aldehyde synthesis
446:groups. The reaction is also known as
6451:Diazoalkane 1,3-dipolar cycloaddition
6355:Vinylcyclopropane (5+2) cycloaddition
6260:Diazoalkane 1,3-dipolar cycloaddition
6032:Hurd–Mori 1,2,3-thiadiazole synthesis
5527:Dowd–Beckwith ring-expansion reaction
4694:Hurd–Mori 1,2,3-thiadiazole synthesis
3607:LFER solvent coefficients (data page)
7:
5262:Sharpless asymmetric dihydroxylation
4499:Methoxymethylenetriphenylphosphorane
2367:Polyhydric alcohols (sugar alcohols)
5387:Allen–Millar–Trippett rearrangement
350:as the stoichiometric oxidant with
6526:Nitrone-olefin (3+2) cycloaddition
6521:Niementowski quinazoline synthesis
6310:Nitrone-olefin (3+2) cycloaddition
6235:Azide-alkyne Huisgen cycloaddition
6097:Niementowski quinazoline synthesis
5852:Azide-alkyne Huisgen cycloaddition
5157:Meerwein–Ponndorf–Verley reduction
4709:Leimgruber–Batcho indole synthesis
442:), resulting in generation of two
392:Soluble transition metal complexes
360:, also a seldom-used method, uses
237:Dess–Martin and related oxidations
61:where the carbon carries a higher
25:
6350:Trimethylenemethane cycloaddition
6052:Johnson–Corey–Chaykovsky reaction
5917:Cadogan–Sundberg indole synthesis
5897:Bohlmann–Rahtz pyridine synthesis
5857:Baeyer–Emmerling indole synthesis
4664:Cadogan–Sundberg indole synthesis
4156:Johnson–Corey–Chaykovsky reaction
3023:2-Methyl-2-propyl-1,3-propanediol
214:(PCC) is the pyridinium salt of .
6446:Cook–Heilbron thiazole synthesis
6275:Hexadehydro Diels–Alder reaction
6102:Niementowski quinoline synthesis
5932:Cook–Heilbron thiazole synthesis
5877:Bischler–Möhlau indole synthesis
5787:Tiffeneau–Demjanov rearrangement
5417:Baker–Venkataraman rearrangement
4575:Horner–Wadsworth–Emmons reaction
4246:Mizoroki-Heck vs. Reductive Heck
4131:Horner–Wadsworth–Emmons reaction
3642:Neighbouring group participation
3270:
3269:
352:tetrapropylammonium perruthenate
5982:Fiesselmann thiophene synthesis
5812:Westphalen–Lettré rearrangement
5792:Vinylcyclopropane rearrangement
5622:Kornblum–DeLaMare rearrangement
5267:Epoxidation of allylic alcohols
5177:Noyori asymmetric hydrogenation
5112:Kornblum–DeLaMare rearrangement
4787:Gallagher–Hollander degradation
3252:Nucleophilic conjugate addition
919:Fournier, H.M. (20 July 1909).
379:oxoammonium-catalyzed oxidation
272:, and an organic base, such as
6441:Chichibabin pyridine synthesis
5927:Chichibabin pyridine synthesis
5887:Blum–Ittah aziridine synthesis
5722:Ring expansion and contraction
3991:Cross dehydrogenative coupling
663:Burton, George et al. (2000).
1:
6411:Bischler–Napieralski reaction
6369:Heterocycle forming reactions
6022:Hemetsberger indole synthesis
5882:Bischler–Napieralski reaction
5797:Wagner–Meerwein rearrangement
5767:Sommelet–Hauser rearrangement
5747:Seyferth–Gilbert homologation
5612:Ireland–Claisen rearrangement
5607:Hofmann–Martius rearrangement
5367:2,3-sigmatropic rearrangement
4982:Corey–Winter olefin synthesis
4907:Barton–McCombie deoxygenation
4550:Corey–Winter olefin synthesis
4504:Seyferth–Gilbert homologation
4371:Seyferth–Gilbert homologation
3223:Fischer–Speier esterification
2155:Propylene glycol methyl ether
1188:10.1016/S0040-4020(01)97963-3
955:10.1016/S0040-4039(00)99393-6
172:is a solution of the same CrO
108:Ketone and aldehyde formation
6516:Lehmstedt–Tanasescu reaction
6476:Gabriel–Colman rearrangement
6431:Bucherer carbazole synthesis
6426:Borsche–Drechsel cyclization
6406:Bernthsen acridine synthesis
6391:Bamberger triazine synthesis
6376:Algar–Flynn–Oyamada reaction
6087:Nazarov cyclization reaction
5952:De Kimpe aziridine synthesis
5907:Bucherer carbazole synthesis
5902:Borsche–Drechsel cyclization
5672:Nazarov cyclization reaction
5652:Meyer–Schuster rearrangement
5582:Gabriel–Colman rearrangement
5332:Wolffenstein–Böters reaction
5217:Reduction of nitro compounds
5067:Grundmann aldehyde synthesis
4872:Algar–Flynn–Oyamada reaction
4281:Olefin conversion technology
4276:Nozaki–Hiyama–Kishi reaction
4071:Gabriel–Colman rearrangement
3961:Claisen-Schmidt condensation
3906:Bouveault aldehyde synthesis
789:Journal of Organic Chemistry
6610:Organic oxidation reactions
6491:Hantzsch pyridine synthesis
6270:Enone–alkene cycloadditions
6092:Nenitzescu indole synthesis
6012:Hantzsch pyridine synthesis
5977:Ferrario–Ackermann reaction
5627:Kowalski ester homologation
5592:Halogen dance rearrangement
5437:Benzilic acid rearrangement
4862:Akabori amino-acid reaction
4822:Von Braun amide degradation
4767:Barbier–Wieland degradation
4719:Nenitzescu indole synthesis
4699:Kharasch–Sosnovsky reaction
4590:Julia–Kocienski olefination
4494:Kowalski ester homologation
4191:Kowalski ester homologation
4166:Julia–Kocienski olefination
3921:Cadiot–Chodkiewicz coupling
3846:Aza-Baylis–Hillman reaction
3791:Acetoacetic ester synthesis
3502:Dynamic binding (chemistry)
3492:Conrotatory and disrotatory
3467:Charge remote fragmentation
1390:4-Methylcyclohexanemethanol
968:"Chromium-based Reagents".
743:Dess, D. B.; Martin, J. C.
684:"Chromium-based Reagents".
6636:
6556:Robinson–Gabriel synthesis
6506:Kröhnke pyridine synthesis
6340:Retro-Diels–Alder reaction
6280:Imine Diels–Alder reaction
6067:Kröhnke pyridine synthesis
5682:Newman–Kwart rearrangement
5657:Mislow–Evans rearrangement
5567:Fischer–Hepp rearrangement
5512:Di-Ď€-methane rearrangement
5292:Stephen aldehyde synthesis
5027:Eschweiler–Clarke reaction
4744:Williamson ether synthesis
4061:Fujiwara–Moritani reaction
3966:Combes quinoline synthesis
3931:Carbonyl olefin metathesis
3632:More O'Ferrall–Jencks plot
3557:Grunwald–Winstein equation
3527:Electron-withdrawing group
3462:Catalytic resonance theory
3228:Williamson ether synthesis
2527:2,4-Dichlorobenzyl alcohol
1458:2-(2-Methoxyethoxy)ethanol
1453:2-(2-Methoxyethoxy)ethanol
614:Niche methods and reagents
550:
321:
6566:Urech hydantoin synthesis
6546:Pomeranz–Fritsch reaction
6471:Fischer oxazole synthesis
6205:1,3-Dipolar cycloaddition
6177:Urech hydantoin synthesis
6147:Reissert indole synthesis
6132:Pomeranz–Fritsch reaction
6062:Knorr quinoline synthesis
5992:Fischer oxazole synthesis
5922:Camps quinoline synthesis
5842:1,3-Dipolar cycloaddition
5742:Semipinacol rearrangement
5717:Ramberg–Bäcklund reaction
5702:Piancatelli rearrangement
5642:McFadyen–Stevens reaction
5397:Alpha-ketol rearrangement
5152:McFadyen–Stevens reaction
5097:Kiliani–Fischer synthesis
5017:Elbs persulfate oxidation
4942:Bouveault–Blanc reduction
4902:Baeyer–Villiger oxidation
4734:Schotten–Baumann reaction
4610:Ramberg–Bäcklund reaction
4489:Kiliani–Fischer synthesis
4331:Ramberg–Bäcklund reaction
4316:Pinacol coupling reaction
4311:Piancatelli rearrangement
4206:Liebeskind–Srogl coupling
4056:Fujimoto–Belleau reaction
3773:List of organic reactions
3637:Negative hyperconjugation
3382:
3324:
3265:
3247:Friedel-Crafts alkylation
3238:Nucleophilic substitution
3218:Nucleophilic substitution
1448:2-(2-Ethoxyethoxy)ethanol
410:Compounds possessing two
212:pyridinium chlorochromate
6541:Pictet–Spengler reaction
6456:Einhorn–Brunner reaction
6421:Boger pyridine synthesis
6315:Oxo-Diels–Alder reaction
6230:Aza-Diels–Alder reaction
6127:Pictet–Spengler reaction
6027:Hofmann–Löffler reaction
6017:Hegedus indole synthesis
5987:Fischer indole synthesis
5862:Bartoli indole synthesis
5817:Willgerodt rearrangement
5647:McLafferty rearrangement
5557:Ferrier carbocyclization
5372:2,3-Wittig rearrangement
5362:1,2-Wittig rearrangement
5202:Parikh–Doering oxidation
5192:Oxygen rebound mechanism
4857:Adkins–Peterson reaction
4749:Yamaguchi esterification
4689:Hegedus indole synthesis
4654:Bartoli indole synthesis
4525:Bamford–Stevens reaction
4441:Weinreb ketone synthesis
4401:Stork enamine alkylation
4176:Knoevenagel condensation
4046:Ferrier carbocyclization
3936:Castro–Stephens coupling
3562:Hammett acidity function
3552:Free-energy relationship
3497:Curtin–Hammett principle
3482:Conformational isomerism
2469:2,2-Dimethylpropan-1-ol
1525:-Diisopropylaminoethanol
731:10.15227/orgsyn.052.0005
6605:Organic redox reactions
6501:Knorr pyrrole synthesis
6436:Bucherer–Bergs reaction
6381:Allan–Robinson reaction
6360:Wagner-Jauregg reaction
6152:Ring-closing metathesis
6077:Larock indole synthesis
6057:Knorr pyrrole synthesis
5912:Bucherer–Bergs reaction
5777:Stieglitz rearrangement
5757:Skattebøl rearrangement
5727:Ring-closing metathesis
5587:Group transfer reaction
5552:Favorskii rearrangement
5492:Cornforth rearrangement
5422:Bamberger rearrangement
5327:Wolff–Kishner reduction
5147:Markó–Lam deoxygenation
5042:Fleming–Tamao oxidation
5037:Fischer–Tropsch process
4724:Oxymercuration reaction
4704:Knorr pyrrole synthesis
4530:Barton–Kellogg reaction
4436:Wagner-Jauregg reaction
4356:Ring-closing metathesis
4346:Reimer–Tiemann reaction
4336:Rauhut–Currier reaction
4251:Nef isocyanide reaction
4211:Malonic ester synthesis
4181:Knorr pyrrole synthesis
4116:High dilution principle
4051:Friedel–Crafts reaction
3986:Cross-coupling reaction
3911:Bucherer–Bergs reaction
3896:Blanc chloromethylation
3886:Blaise ketone synthesis
3861:Baylis–Hillman reaction
3856:Barton–Kellogg reaction
3831:Allan–Robinson reaction
3737:Woodward–Hoffmann rules
3472:Charge-transfer complex
3103:1,3-Difluoro-2-propanol
978:10.1007/0-387-25725-X_1
694:10.1007/0-387-25725-X_1
589:) have been described.
540:Actinomadura luzonensis
243:Dess–Martin periodinane
6466:Feist–Benary synthesis
6240:Bradsher cycloaddition
6210:4+4 Photocycloaddition
6167:Simmons–Smith reaction
6112:Paternò–Büchi reaction
5972:Feist–Benary synthesis
5962:Dieckmann condensation
5712:Pummerer rearrangement
5692:Oxy-Cope rearrangement
5667:Myers allene synthesis
5617:Jacobsen rearrangement
5532:Electrocyclic reaction
5507:Demjanov rearrangement
5462:Buchner ring expansion
5432:Beckmann rearrangement
5412:Aza-Cope rearrangement
5407:Arndt–Eistert reaction
5382:Alkyne zipper reaction
5302:Transfer hydrogenation
5277:Sharpless oxyamination
5252:Selenoxide elimination
5137:Lombardo methylenation
5062:Griesbaum coozonolysis
4972:Corey–Itsuno reduction
4947:Boyland–Sims oxidation
4887:Angeli–Rimini reaction
4535:Boord olefin synthesis
4479:Arndt–Eistert reaction
4471:Homologation reactions
4271:Nitro-Mannich reaction
4186:Kolbe–Schmitt reaction
3996:Cross-coupling partner
3916:Buchner ring expansion
3836:Arndt–Eistert reaction
3602:Kinetic isotope effect
3349:Rearrangement reaction
3108:2,2,2-Trifluoroethanol
1493:Aminoethylethanolamine
1443:2,2,2-Trifluoroethanol
1438:2,2,2-Trichloroethanol
1095:10.1002/ange.200800066
597:
596:Crimmins and DeBaillie
543:
489:Potassium permanganate
484:Potassium permanganate
462:
428:(diacetoxyiodo)benzene
407:
377:Another method is the
374:
332:
283:
140:
117:
76:
6325:Pauson–Khand reaction
6162:Sharpless epoxidation
6117:Pechmann condensation
5997:Friedländer synthesis
5947:Davis–Beirut reaction
5802:Wallach rearrangement
5772:Stevens rearrangement
5707:Pinacol rearrangement
5687:Overman rearrangement
5602:Hofmann rearrangement
5597:Hayashi rearrangement
5562:Ferrier rearrangement
5517:Dimroth rearrangement
5502:Curtius rearrangement
5497:Criegee rearrangement
5477:Claisen rearrangement
5467:Carroll rearrangement
5402:Amadori rearrangement
5392:Allylic rearrangement
5272:Sharpless epoxidation
5007:Dess–Martin oxidation
4932:Bohn–Schmidt reaction
4792:Hofmann rearrangement
4595:Kauffmann olefination
4518:Olefination reactions
4456:Wurtz–Fittig reaction
4291:Palladium–NHC complex
4171:Kauffmann olefination
4126:Homologation reaction
3976:Corey–House synthesis
3956:Claisen rearrangement
3752:Yukawa–Tsuno equation
3712:Swain–Lupton equation
3692:Spherical aromaticity
3627:Möbius–Hückel concept
3412:Aromatic ring current
3374:Substitution reaction
2532:3-Nitrobenzyl alcohol
595:
533:
461:
405:
373:
331:
282:
206:pyridinium dichromate
139:
132:Chromium(VI) reagents
115:
88:, and iodine oxides.
74:
6531:Paal–Knorr synthesis
6401:Barton–Zard reaction
6345:Staudinger synthesis
6295:Ketene cycloaddition
6265:Diels–Alder reaction
6245:Cheletropic reaction
6225:Alkyne trimerisation
6107:Paal–Knorr synthesis
6072:Kulinkovich reaction
6047:Jacobsen epoxidation
5967:Diels–Alder reaction
5762:Smiles rearrangement
5752:Sigmatropic reaction
5637:Lossen rearrangement
5487:Corey–Fuchs reaction
5452:Boekelheide reaction
5447:Bergmann degradation
5377:Achmatowicz reaction
5162:Methionine sulfoxide
4962:Clemmensen reduction
4922:Bergmann degradation
4852:Acyloin condensation
4817:Strecker degradation
4772:Bergmann degradation
4739:Ullmann condensation
4605:Peterson olefination
4580:Hydrazone iodination
4560:Elimination reaction
4461:Zincke–Suhl reaction
4381:Sonogashira coupling
4341:Reformatsky reaction
4301:Peterson olefination
4266:Nierenstein reaction
4196:Kulinkovich reaction
4011:Diels–Alder reaction
3971:Corey–Fuchs reaction
3951:Claisen condensation
3821:Alkyne trimerisation
3796:Acyloin condensation
3762:ÎŁ-bishomoaromaticity
3722:Thorpe–Ingold effect
3334:Elimination reaction
3233:Elimination reaction
1935:1-Heptatetracontanol
1925:1-Pentatetracontanol
1920:1-Tetratetracontanol
1827:(melissyl / myricyl)
1794:(cluytyl / montanyl)
1503:Dimethylethanolamine
1112:. Berlin: Springer.
926:Bull. Soc. Chim. Fr.
286:The by-products are
6551:Prilezhaev reaction
6536:Pellizzari reaction
6215:(4+3) cycloaddition
6182:Van Leusen reaction
6157:Robinson annulation
6142:Pschorr cyclization
6137:Prilezhaev reaction
5867:Bergman cyclization
5822:Wolff rearrangement
5807:Weerman degradation
5697:Pericyclic reaction
5677:Neber rearrangement
5572:Fries rearrangement
5457:Brook rearrangement
5442:Bergman cyclization
5287:Staudinger reaction
5232:Rosenmund reduction
5222:Reductive amination
5187:Oppenauer oxidation
4977:Corey–Kim oxidation
4952:Cannizzaro reaction
4827:Weerman degradation
4802:Isosaccharinic acid
4714:Mukaiyama hydration
4570:Hofmann elimination
4555:Dehydrohalogenation
4540:Chugaev elimination
4361:Robinson annulation
4306:Pfitzinger reaction
4076:Gattermann reaction
4021:Wulff–Dötz reaction
4001:Dakin–West reaction
3926:Carbonyl allylation
3871:Bergman cyclization
3657:Kennedy J. P. Orton
3577:Hammond's postulate
3547:Flippin–Lodge angle
3517:Electromeric effect
3442:Beta-silicon effect
3427:Baker–Nathan effect
3257:Transesterification
2634:Palmitoleyl alcohol
2609:3-Methyl-3-pentanol
2552:Cetostearyl alcohol
2489:3-Methylbutan-2-ol
2484:3-Methylbutan-1-ol
2479:2-Methylbutan-2-ol
2474:2-Methylbutan-1-ol
2258:Monohydric alcohols
2187:3-Methyl-3-pentanol
2177:2-Methylheptan-2-ol
2172:2-Methyl-2-pentanol
1945:1-Nonatetracontanol
1940:1-Octatetracontanol
1930:1-Hexatetracontanol
1863:1-Heptatriacontanol
1853:1-Pentatriacontanol
1847:1-Tetratriacontanol
1533:-Methylethanolamine
1498:Diethylethanolamine
1410:Methylazoxymethanol
1327:Methanol poisoning
801:10.1021/jo01298a066
619:Ruthenium tetroxide
386:sodium hypochlorite
324:Oppenauer oxidation
318:Oppenauer oxidation
158:: a solution of CrO
82:metal oxo complexes
33:is a collection of
6300:McCormack reaction
6250:Conia-ene reaction
6082:Madelung synthesis
5872:Biginelli reaction
5662:Mumm rearrangement
5547:Favorskii reaction
5482:Cope rearrangement
5472:Chan rearrangement
5237:Rubottom oxidation
5167:Miyaura borylation
5132:Lipid peroxidation
5127:Lindgren oxidation
5107:Kornblum oxidation
5102:Kolbe electrolysis
5047:Fukuyama reduction
4957:Carbonyl reduction
4807:Marker degradation
4669:Diazonium compound
4659:Boudouard reaction
4638:Carbon-heteroatom
4565:Grieco elimination
4351:Rieche formylation
4296:Passerini reaction
4226:Meerwein arylation
4146:Hydroxymethylation
4041:Favorskii reaction
3941:Chan rearrangement
3876:Biginelli reaction
3801:Aldol condensation
3647:2-Norbornyl cation
3622:Möbius aromaticity
3617:Markovnikov's rule
3512:Effective molarity
3457:Bürgi–Dunitz angle
3447:Bicycloaromaticity
3152:Carbonyl reduction
3028:Diethylpropanediol
2644:tert-Butyl alcohol
2350:Trihydric alcohols
2192:3-Methyloctan-3-ol
2182:2-Methylhexan-2-ol
2095:3-Methyl-2-butanol
1915:1-Tritetracontanol
1905:1-Hentetracontanol
1873:1-Nonatriacontanol
1868:1-Octatriacontanol
1858:1-Hexatriacontanol
1706:(cetyl / palmityl)
1561:2-Methyl-1-butanol
1400:Cyclohexylmethanol
1259:2-Methyl-1-butanol
832:10.1039/C2GC16344F
598:
544:
469:is converted to a
463:
408:
398:Oxidation of diols
375:
333:
284:
141:
118:
77:
6592:
6591:
6588:
6587:
6584:
6583:
6576:Wohl–Aue reaction
6220:6+4 Cycloaddition
6037:Iodolactonization
5357:1,2-rearrangement
5322:Wohl–Aue reaction
5242:Sabatier reaction
5207:Pinnick oxidation
5172:Mozingo reduction
5117:Leuckart reaction
5072:Haloform reaction
4987:Criegee oxidation
4967:Collins oxidation
4917:Benkeser reaction
4912:Bechamp reduction
4882:Andrussow process
4867:Alcohol oxidation
4777:Edman degradation
4684:Haloform reaction
4633:
4632:
4620:Takai olefination
4585:Julia olefination
4411:Takai olefination
4286:Olefin metathesis
4161:Julia olefination
4086:Grignard reaction
4066:Fukuyama coupling
3981:Coupling reaction
3946:Chan–Lam coupling
3816:Alkyne metathesis
3811:Alkane metathesis
3667:Phosphaethynolate
3572:George S. Hammond
3532:Electronic effect
3487:Conjugated system
3369:Stereospecificity
3364:Stereoselectivity
3329:Addition reaction
3318:organic reactions
3283:
3282:
3206:Alcohol oxidation
3127:Trifluoromethanol
3001:
3000:
2886:
2885:
2639:tert-Amyl alcohol
2619:Linolenyl alcohol
2514:Aromatic alcohols
2455:
2454:
2329:Dihydric alcohols
2242:Triphenylmethanol
2197:Diacetone alcohol
2145:Pinacolyl alcohol
2070:2-Deoxyerythritol
2043:Veratrole alcohol
2023:Propargyl alcohol
2013:Phenethyl alcohol
2003:Nicotinyl alcohol
1998:Neopentyl alcohol
1953:
1952:
1910:1-Dotetracontanol
1842:1-Tritriacontanol
1831:1-Hentriacontanol
1483:2-Mercaptoethanol
1415:Trifluoromethanol
1364:
1363:
1351:Isopropyl alcohol
1279:Phenethyl alcohol
1244:Alcohols found in
1049:10.1021/ja057686l
1037:J. Am. Chem. Soc.
1017:10.1021/jo991292t
943:Tetrahedron Lett.
871:10.1021/ol100290a
795:(10): 2030–2032.
746:J. Am. Chem. Soc.
719:Organic Syntheses
641:Pinnick oxidation
633:partial oxidation
624:Heyns oxidation.
563:chromium trioxide
525:functional groups
523:reacts with many
436:lead tetraacetate
358:FĂ©tizon oxidation
270:dimethylsulfoxide
227:chromium trioxide
39:organic chemistry
31:Alcohol oxidation
27:Chemical reaction
16:(Redirected from
6627:
6620:Carboxylic acids
6615:Primary alcohols
6571:Wenker synthesis
6561:Stollé synthesis
6416:Bobbitt reaction
6386:Auwers synthesis
6330:Povarov reaction
6255:Cyclopropanation
6193:
6187:Wenker synthesis
5942:Darzens reaction
5892:Bobbitt reaction
5737:Schmidt reaction
5542:Enyne metathesis
5317:Whiting reaction
5312:Wharton reaction
5257:Shapiro reaction
5247:Sarett oxidation
5212:Prévost reaction
5022:Emde degradation
4832:Wohl degradation
4812:Ruff degradation
4782:Emde degradation
4679:Grignard reagent
4615:Shapiro reaction
4600:McMurry reaction
4467:
4431:Ullmann reaction
4396:Stollé synthesis
4386:Stetter reaction
4376:Shapiro reaction
4366:Sakurai reaction
4261:Negishi coupling
4241:Minisci reaction
4236:Michael reaction
4221:McMurry reaction
4216:Mannich reaction
4096:Hammick reaction
4091:Grignard reagent
4031:Enyne metathesis
4016:Doebner reaction
4006:Darzens reaction
3851:Barbier reaction
3841:Auwers synthesis
3768:
3742:Woodward's rules
3707:Superaromaticity
3697:Spiroaromaticity
3597:Inductive effect
3592:Hyperconjugation
3567:Hammett equation
3507:Edwards equation
3359:Regioselectivity
3310:
3303:
3296:
3287:
3273:
3272:
2895:
2891:Terpene alcohols
2676:Methylene glycol
2659:
2624:Linoleyl alcohol
2567:Myristyl alcohol
2394:Propylene glycol
2341:Propylene glycol
2255:
2237:Triphenylethanol
2150:Pirkle's alcohol
2135:Diphenylmethanol
2038:Vanillyl alcohol
2008:Perillyl alcohol
1988:Furfuryl alcohol
1978:Cinnamyl alcohol
1836:1-Dotriacontanol
1488:2-Methoxyethanol
1378:
1246:alcoholic drinks
1240:
1222:
1215:
1208:
1199:
1192:
1191:
1171:
1165:
1151:
1145:
1130:
1124:
1123:
1105:
1099:
1098:
1077:
1071:
1070:
1060:
1027:
1021:
1020:
998:
992:
991:
965:
959:
958:
937:
931:
930:
916:
910:
909:
905:C. R. Acad. Sci.
899:
893:
892:
882:
850:
844:
843:
811:
805:
804:
784:
778:
763:
757:
741:
735:
734:
714:
708:
707:
681:
675:
661:
561:, prepared from
420:sodium periodate
362:silver carbonate
288:dimethyl sulfide
225:, a solution of
189:, featuring the
156:Sarett's reagent
94:aldehyde hydrate
55:carboxylic acids
21:
6635:
6634:
6630:
6629:
6628:
6626:
6625:
6624:
6595:
6594:
6593:
6580:
6481:Gewald reaction
6364:
6191:
6172:Skraup reaction
6007:Graham reaction
6002:Gewald reaction
5833:
5826:
5348:
5341:
5297:Swern oxidation
5282:Stahl oxidation
5227:Riley oxidation
5182:Omega oxidation
5142:Luche reduction
5092:Jones oxidation
5057:Glycol cleavage
5052:Ganem oxidation
4997:Davis oxidation
4992:Dakin oxidation
4927:Birch reduction
4877:Amide reduction
4843:
4836:
4797:Hooker reaction
4759:
4753:
4641:
4639:
4629:
4625:Wittig reaction
4513:
4509:Wittig reaction
4484:Hooker reaction
4465:
4446:Wittig reaction
4421:Thorpe reaction
4406:Suzuki reaction
4391:Stille reaction
4326:Quelet reaction
4201:Kumada coupling
4151:Ivanov reaction
4141:Hydrovinylation
4121:Hiyama coupling
4081:Glaser coupling
3891:Blaise reaction
3881:Bingel reaction
3866:Benary reaction
3783:
3781:
3775:
3766:
3662:Passive binding
3582:Homoaromaticity
3432:Baldwin's rules
3407:Antiaromaticity
3402:Anomeric effect
3378:
3320:
3314:
3284:
3279:
3261:
3211:Glycol cleavage
3184:
3180:Ziegler process
3131:
3113:2-Fluoroethanol
3089:
3053:
3037:
3033:Ethylene glycol
3018:1,5-Pentanediol
2997:
2985:
2979:
2952:
2946:
2899:
2882:
2846:Glycylglycitols
2841:
2829:
2823:
2811:
2805:
2801:
2791:
2781:
2771:
2761:
2751:
2741:
2731:
2721:
2711:
2701:
2691:
2686:Ethylene glycol
2681:
2669:
2665:
2648:
2599:
2597:
2591:
2542:
2536:
2508:
2451:
2447:
2437:
2423:
2413:
2399:
2385:
2380:Ethylene glycol
2375:Pentaerythritol
2361:
2345:
2336:Ethylene glycol
2324:
2320:
2310:
2300:
2290:
2280:
2270:
2251:Hydric alcohols
2246:
2164:
2158:
2060:1-Phenylethanol
2053:
2047:
2028:Salicyl alcohol
1993:Isoamyl alcohol
1949:
1900:1-Tetracontanol
1893:
1889:
1885:
1883:
1877:
1818:
1814:
1810:
1808:
1802:
1741:
1737:
1733:
1731:
1725:
1663:
1659:
1655:
1653:
1647:
1594:
1590:
1586:
1584:
1578:
1547:
1543:Tribromoethanol
1478:2-Fluoroethanol
1473:2-Ethoxyethanol
1468:2-Chloroethanol
1463:2-Butoxyethanol
1419:
1405:Methoxymethanol
1371:
1360:
1337:
1310:Medical alcohol
1304:
1269:Isoamyl alcohol
1245:
1231:
1226:
1196:
1195:
1173:
1172:
1168:
1152:
1148:
1131:
1127:
1120:
1107:
1106:
1102:
1079:
1078:
1074:
1029:
1028:
1024:
1000:
999:
995:
988:
967:
966:
962:
939:
938:
934:
918:
917:
913:
901:
900:
896:
859:Organic Letters
852:
851:
847:
820:Green Chemistry
813:
812:
808:
786:
785:
781:
764:
760:
742:
738:
716:
715:
711:
704:
683:
682:
678:
662:
658:
653:
645:sodium chlorite
616:
603:
588:
584:
568:
555:
553:Jones oxidation
549:
547:Jones oxidation
537:
522:
498:
494:
486:
475:oxidation state
471:carboxylic acid
467:primary alcohol
456:
448:glycol cleavage
441:
433:
425:
400:
354:as a catalyst.
341:
326:
320:
313:
309:
305:
296:carbon monoxide
293:
266:oxalyl chloride
262:Swern oxidation
259:
257:Swern oxidation
247:dichloromethane
239:
200:
196:
179:
175:
170:Collins reagent
165:
161:
150:
146:
134:
110:
103:
100:-diol, R-CH(OH)
63:oxidation state
28:
23:
22:
15:
12:
11:
5:
6633:
6631:
6623:
6622:
6617:
6612:
6607:
6597:
6596:
6590:
6589:
6586:
6585:
6582:
6581:
6579:
6578:
6573:
6568:
6563:
6558:
6553:
6548:
6543:
6538:
6533:
6528:
6523:
6518:
6513:
6508:
6503:
6498:
6493:
6488:
6486:Hantzsch ester
6483:
6478:
6473:
6468:
6463:
6458:
6453:
6448:
6443:
6438:
6433:
6428:
6423:
6418:
6413:
6408:
6403:
6398:
6396:Banert cascade
6393:
6388:
6383:
6378:
6372:
6370:
6366:
6365:
6363:
6362:
6357:
6352:
6347:
6342:
6337:
6335:Prato reaction
6332:
6327:
6322:
6317:
6312:
6307:
6302:
6297:
6292:
6287:
6282:
6277:
6272:
6267:
6262:
6257:
6252:
6247:
6242:
6237:
6232:
6227:
6222:
6217:
6212:
6207:
6201:
6199:
6190:
6189:
6184:
6179:
6174:
6169:
6164:
6159:
6154:
6149:
6144:
6139:
6134:
6129:
6124:
6119:
6114:
6109:
6104:
6099:
6094:
6089:
6084:
6079:
6074:
6069:
6064:
6059:
6054:
6049:
6044:
6039:
6034:
6029:
6024:
6019:
6014:
6009:
6004:
5999:
5994:
5989:
5984:
5979:
5974:
5969:
5964:
5959:
5954:
5949:
5944:
5939:
5934:
5929:
5924:
5919:
5914:
5909:
5904:
5899:
5894:
5889:
5884:
5879:
5874:
5869:
5864:
5859:
5854:
5849:
5844:
5838:
5836:
5828:
5827:
5825:
5824:
5819:
5814:
5809:
5804:
5799:
5794:
5789:
5784:
5779:
5774:
5769:
5764:
5759:
5754:
5749:
5744:
5739:
5734:
5729:
5724:
5719:
5714:
5709:
5704:
5699:
5694:
5689:
5684:
5679:
5674:
5669:
5664:
5659:
5654:
5649:
5644:
5639:
5634:
5629:
5624:
5619:
5614:
5609:
5604:
5599:
5594:
5589:
5584:
5579:
5574:
5569:
5564:
5559:
5554:
5549:
5544:
5539:
5534:
5529:
5524:
5519:
5514:
5509:
5504:
5499:
5494:
5489:
5484:
5479:
5474:
5469:
5464:
5459:
5454:
5449:
5444:
5439:
5434:
5429:
5427:Banert cascade
5424:
5419:
5414:
5409:
5404:
5399:
5394:
5389:
5384:
5379:
5374:
5369:
5364:
5359:
5353:
5351:
5347:Rearrangement
5343:
5342:
5340:
5339:
5337:Zinin reaction
5334:
5329:
5324:
5319:
5314:
5309:
5307:Wacker process
5304:
5299:
5294:
5289:
5284:
5279:
5274:
5269:
5264:
5259:
5254:
5249:
5244:
5239:
5234:
5229:
5224:
5219:
5214:
5209:
5204:
5199:
5194:
5189:
5184:
5179:
5174:
5169:
5164:
5159:
5154:
5149:
5144:
5139:
5134:
5129:
5124:
5119:
5114:
5109:
5104:
5099:
5094:
5089:
5084:
5082:Hydrogenolysis
5079:
5074:
5069:
5064:
5059:
5054:
5049:
5044:
5039:
5034:
5032:Étard reaction
5029:
5024:
5019:
5014:
5009:
5004:
4999:
4994:
4989:
4984:
4979:
4974:
4969:
4964:
4959:
4954:
4949:
4944:
4939:
4937:Bosch reaction
4934:
4929:
4924:
4919:
4914:
4909:
4904:
4899:
4894:
4889:
4884:
4879:
4874:
4869:
4864:
4859:
4854:
4848:
4846:
4842:Organic redox
4838:
4837:
4835:
4834:
4829:
4824:
4819:
4814:
4809:
4804:
4799:
4794:
4789:
4784:
4779:
4774:
4769:
4763:
4761:
4755:
4754:
4752:
4751:
4746:
4741:
4736:
4731:
4726:
4721:
4716:
4711:
4706:
4701:
4696:
4691:
4686:
4681:
4676:
4674:Esterification
4671:
4666:
4661:
4656:
4651:
4645:
4643:
4635:
4634:
4631:
4630:
4628:
4627:
4622:
4617:
4612:
4607:
4602:
4597:
4592:
4587:
4582:
4577:
4572:
4567:
4562:
4557:
4552:
4547:
4542:
4537:
4532:
4527:
4521:
4519:
4515:
4514:
4512:
4511:
4506:
4501:
4496:
4491:
4486:
4481:
4475:
4473:
4464:
4463:
4458:
4453:
4451:Wurtz reaction
4448:
4443:
4438:
4433:
4428:
4423:
4418:
4413:
4408:
4403:
4398:
4393:
4388:
4383:
4378:
4373:
4368:
4363:
4358:
4353:
4348:
4343:
4338:
4333:
4328:
4323:
4321:Prins reaction
4318:
4313:
4308:
4303:
4298:
4293:
4288:
4283:
4278:
4273:
4268:
4263:
4258:
4253:
4248:
4243:
4238:
4233:
4228:
4223:
4218:
4213:
4208:
4203:
4198:
4193:
4188:
4183:
4178:
4173:
4168:
4163:
4158:
4153:
4148:
4143:
4138:
4136:Hydrocyanation
4133:
4128:
4123:
4118:
4113:
4108:
4106:Henry reaction
4103:
4098:
4093:
4088:
4083:
4078:
4073:
4068:
4063:
4058:
4053:
4048:
4043:
4038:
4033:
4028:
4023:
4018:
4013:
4008:
4003:
3998:
3993:
3988:
3983:
3978:
3973:
3968:
3963:
3958:
3953:
3948:
3943:
3938:
3933:
3928:
3923:
3918:
3913:
3908:
3903:
3898:
3893:
3888:
3883:
3878:
3873:
3868:
3863:
3858:
3853:
3848:
3843:
3838:
3833:
3828:
3823:
3818:
3813:
3808:
3806:Aldol reaction
3803:
3798:
3793:
3787:
3785:
3780:Carbon-carbon
3777:
3776:
3771:
3765:
3764:
3759:
3757:Zaitsev's rule
3754:
3749:
3744:
3739:
3734:
3729:
3724:
3719:
3714:
3709:
3704:
3702:Steric effects
3699:
3694:
3689:
3684:
3679:
3674:
3669:
3664:
3659:
3654:
3649:
3644:
3639:
3634:
3629:
3624:
3619:
3614:
3609:
3604:
3599:
3594:
3589:
3584:
3579:
3574:
3569:
3564:
3559:
3554:
3549:
3544:
3539:
3534:
3529:
3524:
3519:
3514:
3509:
3504:
3499:
3494:
3489:
3484:
3479:
3474:
3469:
3464:
3459:
3454:
3449:
3444:
3439:
3434:
3429:
3424:
3419:
3414:
3409:
3404:
3399:
3394:
3389:
3383:
3380:
3379:
3377:
3376:
3371:
3366:
3361:
3356:
3354:Redox reaction
3351:
3346:
3341:
3339:Polymerization
3336:
3331:
3325:
3322:
3321:
3315:
3313:
3312:
3305:
3298:
3290:
3281:
3280:
3278:
3277:
3266:
3263:
3262:
3260:
3259:
3254:
3249:
3244:
3242:carbonyl group
3235:
3230:
3225:
3220:
3215:
3214:
3213:
3203:
3198:
3192:
3190:
3186:
3185:
3183:
3182:
3177:
3168:
3159:
3157:Ether cleavage
3154:
3149:
3139:
3137:
3133:
3132:
3130:
3129:
3124:
3122:-butyl alcohol
3115:
3110:
3105:
3099:
3097:
3095:Fluoroalcohols
3091:
3090:
3088:
3087:
3082:
3077:
3072:
3067:
3061:
3059:
3055:
3054:
3052:
3051:
3045:
3043:
3039:
3038:
3036:
3035:
3030:
3025:
3020:
3015:
3013:1,4-Butanediol
3009:
3007:
3003:
3002:
2999:
2998:
2996:
2995:
2989:
2987:
2981:
2980:
2978:
2977:
2972:
2967:
2962:
2956:
2954:
2948:
2947:
2945:
2944:
2939:
2934:
2929:
2924:
2919:
2914:
2909:
2903:
2901:
2892:
2888:
2887:
2884:
2883:
2881:
2880:
2875:
2873:Maltotetraitol
2870:
2865:
2860:
2855:
2849:
2847:
2843:
2842:
2840:
2839:
2833:
2831:
2825:
2824:
2822:
2821:
2815:
2813:
2807:
2806:
2804:
2803:
2799:
2793:
2789:
2783:
2779:
2773:
2769:
2763:
2759:
2753:
2749:
2743:
2739:
2733:
2729:
2723:
2719:
2713:
2709:
2703:
2699:
2693:
2689:
2683:
2679:
2672:
2670:
2667:
2663:
2656:
2654:Sugar alcohols
2650:
2649:
2647:
2646:
2641:
2636:
2631:
2626:
2621:
2616:
2614:Erucyl alcohol
2611:
2605:
2603:
2601:fatty alcohols
2593:
2592:
2590:
2589:
2584:
2579:
2574:
2569:
2564:
2562:Lauryl alcohol
2559:
2554:
2548:
2546:
2544:fatty alcohols
2538:
2537:
2535:
2534:
2529:
2524:
2522:Benzyl alcohol
2518:
2516:
2510:
2509:
2507:
2506:
2501:
2496:
2491:
2486:
2481:
2476:
2471:
2465:
2463:
2457:
2456:
2453:
2452:
2450:
2449:
2445:
2439:
2435:
2425:
2421:
2415:
2411:
2401:
2397:
2387:
2383:
2377:
2371:
2369:
2363:
2362:
2360:
2359:
2353:
2351:
2347:
2346:
2344:
2343:
2338:
2332:
2330:
2326:
2325:
2323:
2322:
2318:
2312:
2308:
2302:
2298:
2292:
2288:
2282:
2278:
2272:
2268:
2261:
2259:
2252:
2248:
2247:
2245:
2244:
2239:
2234:
2232:-Butyl alcohol
2226:
2218:
2216:-butyl alcohol
2209:
2207:Methylpentynol
2204:
2199:
2194:
2189:
2184:
2179:
2174:
2168:
2166:
2160:
2159:
2157:
2152:
2147:
2142:
2137:
2132:
2127:
2122:
2117:
2112:
2107:
2102:
2097:
2092:
2087:
2082:
2077:
2072:
2067:
2062:
2057:
2055:
2049:
2048:
2046:
2045:
2040:
2035:
2030:
2025:
2020:
2015:
2010:
2005:
2000:
1995:
1990:
1985:
1983:Crotyl alcohol
1980:
1975:
1973:Benzyl alcohol
1970:
1968:Anisyl alcohol
1965:
1960:
1958:2-Ethylhexanol
1954:
1951:
1950:
1948:
1947:
1942:
1937:
1932:
1927:
1922:
1917:
1912:
1907:
1902:
1896:
1894:
1891:
1887:
1882:Straight-chain
1879:
1878:
1876:
1875:
1870:
1865:
1860:
1855:
1850:
1844:
1839:
1833:
1828:
1825:1-Triacontanol
1821:
1819:
1816:
1812:
1807:Straight-chain
1804:
1803:
1801:
1800:
1795:
1789:
1787:1-Heptacosanol
1784:
1778:
1776:1-Pentacosanol
1773:
1770:1-Tetracosanol
1767:
1762:
1756:
1754:1-Heneicosanol
1751:
1744:
1742:
1739:
1735:
1730:Straight-chain
1727:
1726:
1724:
1723:
1718:
1712:
1710:1-Heptadecanol
1707:
1701:
1699:1-Pentadecanol
1696:
1693:1-Tetradecanol
1690:
1685:
1679:
1673:
1666:
1664:
1661:
1657:
1652:Straight-chain
1649:
1648:
1646:
1645:
1639:
1633:
1628:
1623:
1618:
1613:
1608:
1603:
1597:
1595:
1592:
1588:
1583:Straight-chain
1580:
1579:
1577:
1576:
1568:
1563:
1557:
1555:
1549:
1548:
1546:
1545:
1540:
1538:Phenoxyethanol
1535:
1527:
1515:
1510:
1505:
1500:
1495:
1490:
1485:
1480:
1475:
1470:
1465:
1460:
1455:
1450:
1445:
1440:
1435:
1433:1-Aminoethanol
1429:
1427:
1421:
1420:
1418:
1417:
1412:
1407:
1402:
1397:
1392:
1386:
1384:
1375:
1366:
1365:
1362:
1361:
1359:
1358:
1353:
1347:
1345:
1343:Toxic alcohols
1339:
1338:
1336:
1335:
1334:
1333:
1325:
1323:Methylpentynol
1320:
1314:
1312:
1306:
1305:
1303:
1302:
1297:
1295:-Butyl alcohol
1289:
1281:
1276:
1271:
1266:
1261:
1256:
1250:
1248:
1237:
1236:By consumption
1233:
1232:
1227:
1225:
1224:
1217:
1210:
1202:
1194:
1193:
1166:
1146:
1125:
1118:
1100:
1072:
1043:(15): 4936–7.
1022:
993:
986:
960:
932:
911:
894:
845:
826:(3): 547–564.
806:
779:
758:
736:
709:
702:
676:
655:
654:
652:
649:
615:
612:
602:
599:
586:
582:
569:) and aqueous
566:
557:The so-called
551:Main article:
548:
545:
535:
520:
496:
492:
485:
482:
455:
452:
439:
431:
423:
399:
396:
384:Additionally,
340:
337:
322:Main article:
319:
316:
311:
307:
303:
300:carbon dioxide
291:
258:
255:
238:
235:
216:
215:
209:
198:
194:
183:
182:
177:
173:
167:
163:
159:
148:
144:
133:
130:
109:
106:
101:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
6632:
6621:
6618:
6616:
6613:
6611:
6608:
6606:
6603:
6602:
6600:
6577:
6574:
6572:
6569:
6567:
6564:
6562:
6559:
6557:
6554:
6552:
6549:
6547:
6544:
6542:
6539:
6537:
6534:
6532:
6529:
6527:
6524:
6522:
6519:
6517:
6514:
6512:
6509:
6507:
6504:
6502:
6499:
6497:
6496:Herz reaction
6494:
6492:
6489:
6487:
6484:
6482:
6479:
6477:
6474:
6472:
6469:
6467:
6464:
6462:
6459:
6457:
6454:
6452:
6449:
6447:
6444:
6442:
6439:
6437:
6434:
6432:
6429:
6427:
6424:
6422:
6419:
6417:
6414:
6412:
6409:
6407:
6404:
6402:
6399:
6397:
6394:
6392:
6389:
6387:
6384:
6382:
6379:
6377:
6374:
6373:
6371:
6367:
6361:
6358:
6356:
6353:
6351:
6348:
6346:
6343:
6341:
6338:
6336:
6333:
6331:
6328:
6326:
6323:
6321:
6318:
6316:
6313:
6311:
6308:
6306:
6303:
6301:
6298:
6296:
6293:
6291:
6288:
6286:
6283:
6281:
6278:
6276:
6273:
6271:
6268:
6266:
6263:
6261:
6258:
6256:
6253:
6251:
6248:
6246:
6243:
6241:
6238:
6236:
6233:
6231:
6228:
6226:
6223:
6221:
6218:
6216:
6213:
6211:
6208:
6206:
6203:
6202:
6200:
6198:
6197:Cycloaddition
6194:
6188:
6185:
6183:
6180:
6178:
6175:
6173:
6170:
6168:
6165:
6163:
6160:
6158:
6155:
6153:
6150:
6148:
6145:
6143:
6140:
6138:
6135:
6133:
6130:
6128:
6125:
6123:
6120:
6118:
6115:
6113:
6110:
6108:
6105:
6103:
6100:
6098:
6095:
6093:
6090:
6088:
6085:
6083:
6080:
6078:
6075:
6073:
6070:
6068:
6065:
6063:
6060:
6058:
6055:
6053:
6050:
6048:
6045:
6043:
6042:Isay reaction
6040:
6038:
6035:
6033:
6030:
6028:
6025:
6023:
6020:
6018:
6015:
6013:
6010:
6008:
6005:
6003:
6000:
5998:
5995:
5993:
5990:
5988:
5985:
5983:
5980:
5978:
5975:
5973:
5970:
5968:
5965:
5963:
5960:
5958:
5955:
5953:
5950:
5948:
5945:
5943:
5940:
5938:
5937:Cycloaddition
5935:
5933:
5930:
5928:
5925:
5923:
5920:
5918:
5915:
5913:
5910:
5908:
5905:
5903:
5900:
5898:
5895:
5893:
5890:
5888:
5885:
5883:
5880:
5878:
5875:
5873:
5870:
5868:
5865:
5863:
5860:
5858:
5855:
5853:
5850:
5848:
5845:
5843:
5840:
5839:
5837:
5835:
5832:Ring forming
5829:
5823:
5820:
5818:
5815:
5813:
5810:
5808:
5805:
5803:
5800:
5798:
5795:
5793:
5790:
5788:
5785:
5783:
5780:
5778:
5775:
5773:
5770:
5768:
5765:
5763:
5760:
5758:
5755:
5753:
5750:
5748:
5745:
5743:
5740:
5738:
5735:
5733:
5732:Rupe reaction
5730:
5728:
5725:
5723:
5720:
5718:
5715:
5713:
5710:
5708:
5705:
5703:
5700:
5698:
5695:
5693:
5690:
5688:
5685:
5683:
5680:
5678:
5675:
5673:
5670:
5668:
5665:
5663:
5660:
5658:
5655:
5653:
5650:
5648:
5645:
5643:
5640:
5638:
5635:
5633:
5630:
5628:
5625:
5623:
5620:
5618:
5615:
5613:
5610:
5608:
5605:
5603:
5600:
5598:
5595:
5593:
5590:
5588:
5585:
5583:
5580:
5578:
5575:
5573:
5570:
5568:
5565:
5563:
5560:
5558:
5555:
5553:
5550:
5548:
5545:
5543:
5540:
5538:
5535:
5533:
5530:
5528:
5525:
5523:
5520:
5518:
5515:
5513:
5510:
5508:
5505:
5503:
5500:
5498:
5495:
5493:
5490:
5488:
5485:
5483:
5480:
5478:
5475:
5473:
5470:
5468:
5465:
5463:
5460:
5458:
5455:
5453:
5450:
5448:
5445:
5443:
5440:
5438:
5435:
5433:
5430:
5428:
5425:
5423:
5420:
5418:
5415:
5413:
5410:
5408:
5405:
5403:
5400:
5398:
5395:
5393:
5390:
5388:
5385:
5383:
5380:
5378:
5375:
5373:
5370:
5368:
5365:
5363:
5360:
5358:
5355:
5354:
5352:
5350:
5344:
5338:
5335:
5333:
5330:
5328:
5325:
5323:
5320:
5318:
5315:
5313:
5310:
5308:
5305:
5303:
5300:
5298:
5295:
5293:
5290:
5288:
5285:
5283:
5280:
5278:
5275:
5273:
5270:
5268:
5265:
5263:
5260:
5258:
5255:
5253:
5250:
5248:
5245:
5243:
5240:
5238:
5235:
5233:
5230:
5228:
5225:
5223:
5220:
5218:
5215:
5213:
5210:
5208:
5205:
5203:
5200:
5198:
5195:
5193:
5190:
5188:
5185:
5183:
5180:
5178:
5175:
5173:
5170:
5168:
5165:
5163:
5160:
5158:
5155:
5153:
5150:
5148:
5145:
5143:
5140:
5138:
5135:
5133:
5130:
5128:
5125:
5123:
5122:Ley oxidation
5120:
5118:
5115:
5113:
5110:
5108:
5105:
5103:
5100:
5098:
5095:
5093:
5090:
5088:
5087:Hydroxylation
5085:
5083:
5080:
5078:
5077:Hydrogenation
5075:
5073:
5070:
5068:
5065:
5063:
5060:
5058:
5055:
5053:
5050:
5048:
5045:
5043:
5040:
5038:
5035:
5033:
5030:
5028:
5025:
5023:
5020:
5018:
5015:
5013:
5012:DNA oxidation
5010:
5008:
5005:
5003:
5002:Deoxygenation
5000:
4998:
4995:
4993:
4990:
4988:
4985:
4983:
4980:
4978:
4975:
4973:
4970:
4968:
4965:
4963:
4960:
4958:
4955:
4953:
4950:
4948:
4945:
4943:
4940:
4938:
4935:
4933:
4930:
4928:
4925:
4923:
4920:
4918:
4915:
4913:
4910:
4908:
4905:
4903:
4900:
4898:
4895:
4893:
4892:Aromatization
4890:
4888:
4885:
4883:
4880:
4878:
4875:
4873:
4870:
4868:
4865:
4863:
4860:
4858:
4855:
4853:
4850:
4849:
4847:
4845:
4839:
4833:
4830:
4828:
4825:
4823:
4820:
4818:
4815:
4813:
4810:
4808:
4805:
4803:
4800:
4798:
4795:
4793:
4790:
4788:
4785:
4783:
4780:
4778:
4775:
4773:
4770:
4768:
4765:
4764:
4762:
4756:
4750:
4747:
4745:
4742:
4740:
4737:
4735:
4732:
4730:
4729:Reed reaction
4727:
4725:
4722:
4720:
4717:
4715:
4712:
4710:
4707:
4705:
4702:
4700:
4697:
4695:
4692:
4690:
4687:
4685:
4682:
4680:
4677:
4675:
4672:
4670:
4667:
4665:
4662:
4660:
4657:
4655:
4652:
4650:
4647:
4646:
4644:
4640:bond forming
4636:
4626:
4623:
4621:
4618:
4616:
4613:
4611:
4608:
4606:
4603:
4601:
4598:
4596:
4593:
4591:
4588:
4586:
4583:
4581:
4578:
4576:
4573:
4571:
4568:
4566:
4563:
4561:
4558:
4556:
4553:
4551:
4548:
4546:
4545:Cope reaction
4543:
4541:
4538:
4536:
4533:
4531:
4528:
4526:
4523:
4522:
4520:
4516:
4510:
4507:
4505:
4502:
4500:
4497:
4495:
4492:
4490:
4487:
4485:
4482:
4480:
4477:
4476:
4474:
4472:
4468:
4462:
4459:
4457:
4454:
4452:
4449:
4447:
4444:
4442:
4439:
4437:
4434:
4432:
4429:
4427:
4424:
4422:
4419:
4417:
4414:
4412:
4409:
4407:
4404:
4402:
4399:
4397:
4394:
4392:
4389:
4387:
4384:
4382:
4379:
4377:
4374:
4372:
4369:
4367:
4364:
4362:
4359:
4357:
4354:
4352:
4349:
4347:
4344:
4342:
4339:
4337:
4334:
4332:
4329:
4327:
4324:
4322:
4319:
4317:
4314:
4312:
4309:
4307:
4304:
4302:
4299:
4297:
4294:
4292:
4289:
4287:
4284:
4282:
4279:
4277:
4274:
4272:
4269:
4267:
4264:
4262:
4259:
4257:
4256:Nef synthesis
4254:
4252:
4249:
4247:
4244:
4242:
4239:
4237:
4234:
4232:
4231:Methylenation
4229:
4227:
4224:
4222:
4219:
4217:
4214:
4212:
4209:
4207:
4204:
4202:
4199:
4197:
4194:
4192:
4189:
4187:
4184:
4182:
4179:
4177:
4174:
4172:
4169:
4167:
4164:
4162:
4159:
4157:
4154:
4152:
4149:
4147:
4144:
4142:
4139:
4137:
4134:
4132:
4129:
4127:
4124:
4122:
4119:
4117:
4114:
4112:
4109:
4107:
4104:
4102:
4101:Heck reaction
4099:
4097:
4094:
4092:
4089:
4087:
4084:
4082:
4079:
4077:
4074:
4072:
4069:
4067:
4064:
4062:
4059:
4057:
4054:
4052:
4049:
4047:
4044:
4042:
4039:
4037:
4034:
4032:
4029:
4027:
4024:
4022:
4019:
4017:
4014:
4012:
4009:
4007:
4004:
4002:
3999:
3997:
3994:
3992:
3989:
3987:
3984:
3982:
3979:
3977:
3974:
3972:
3969:
3967:
3964:
3962:
3959:
3957:
3954:
3952:
3949:
3947:
3944:
3942:
3939:
3937:
3934:
3932:
3929:
3927:
3924:
3922:
3919:
3917:
3914:
3912:
3909:
3907:
3904:
3902:
3899:
3897:
3894:
3892:
3889:
3887:
3884:
3882:
3879:
3877:
3874:
3872:
3869:
3867:
3864:
3862:
3859:
3857:
3854:
3852:
3849:
3847:
3844:
3842:
3839:
3837:
3834:
3832:
3829:
3827:
3824:
3822:
3819:
3817:
3814:
3812:
3809:
3807:
3804:
3802:
3799:
3797:
3794:
3792:
3789:
3788:
3786:
3782:bond forming
3778:
3774:
3769:
3763:
3760:
3758:
3755:
3753:
3750:
3748:
3747:Y-aromaticity
3745:
3743:
3740:
3738:
3735:
3733:
3732:Walsh diagram
3730:
3728:
3725:
3723:
3720:
3718:
3717:Taft equation
3715:
3713:
3710:
3708:
3705:
3703:
3700:
3698:
3695:
3693:
3690:
3688:
3687:ÎŁ-aromaticity
3685:
3683:
3680:
3678:
3675:
3673:
3670:
3668:
3665:
3663:
3660:
3658:
3655:
3653:
3650:
3648:
3645:
3643:
3640:
3638:
3635:
3633:
3630:
3628:
3625:
3623:
3620:
3618:
3615:
3613:
3612:Marcus theory
3610:
3608:
3605:
3603:
3600:
3598:
3595:
3593:
3590:
3588:
3587:HĂĽckel's rule
3585:
3583:
3580:
3578:
3575:
3573:
3570:
3568:
3565:
3563:
3560:
3558:
3555:
3553:
3550:
3548:
3545:
3543:
3542:Evelyn effect
3540:
3538:
3535:
3533:
3530:
3528:
3525:
3523:
3522:Electron-rich
3520:
3518:
3515:
3513:
3510:
3508:
3505:
3503:
3500:
3498:
3495:
3493:
3490:
3488:
3485:
3483:
3480:
3478:
3475:
3473:
3470:
3468:
3465:
3463:
3460:
3458:
3455:
3453:
3450:
3448:
3445:
3443:
3440:
3438:
3437:Bema Hapothle
3435:
3433:
3430:
3428:
3425:
3423:
3420:
3418:
3415:
3413:
3410:
3408:
3405:
3403:
3400:
3398:
3395:
3393:
3390:
3388:
3385:
3384:
3381:
3375:
3372:
3370:
3367:
3365:
3362:
3360:
3357:
3355:
3352:
3350:
3347:
3345:
3342:
3340:
3337:
3335:
3332:
3330:
3327:
3326:
3323:
3319:
3311:
3306:
3304:
3299:
3297:
3292:
3291:
3288:
3276:
3268:
3267:
3264:
3258:
3255:
3253:
3250:
3248:
3245:
3243:
3239:
3236:
3234:
3231:
3229:
3226:
3224:
3221:
3219:
3216:
3212:
3209:
3208:
3207:
3204:
3202:
3199:
3197:
3196:Deprotonation
3194:
3193:
3191:
3187:
3181:
3178:
3176:
3172:
3169:
3167:
3163:
3160:
3158:
3155:
3153:
3150:
3148:
3144:
3141:
3140:
3138:
3134:
3128:
3125:
3123:
3121:
3116:
3114:
3111:
3109:
3106:
3104:
3101:
3100:
3098:
3096:
3092:
3086:
3083:
3081:
3078:
3076:
3073:
3071:
3068:
3066:
3063:
3062:
3060:
3056:
3050:
3047:
3046:
3044:
3040:
3034:
3031:
3029:
3026:
3024:
3021:
3019:
3016:
3014:
3011:
3010:
3008:
3004:
2994:
2991:
2990:
2988:
2982:
2976:
2973:
2971:
2968:
2966:
2963:
2961:
2958:
2957:
2955:
2951:Sesquiterpene
2949:
2943:
2940:
2938:
2935:
2933:
2930:
2928:
2925:
2923:
2920:
2918:
2915:
2913:
2910:
2908:
2905:
2904:
2902:
2896:
2893:
2889:
2879:
2876:
2874:
2871:
2869:
2866:
2864:
2861:
2859:
2856:
2854:
2851:
2850:
2848:
2844:
2838:
2835:
2834:
2832:
2826:
2820:
2817:
2816:
2814:
2808:
2797:
2794:
2787:
2784:
2777:
2774:
2767:
2764:
2757:
2754:
2747:
2744:
2737:
2734:
2727:
2724:
2717:
2714:
2707:
2704:
2697:
2694:
2687:
2684:
2677:
2674:
2673:
2671:
2660:
2657:
2655:
2651:
2645:
2642:
2640:
2637:
2635:
2632:
2630:
2629:Oleyl alcohol
2627:
2625:
2622:
2620:
2617:
2615:
2612:
2610:
2607:
2606:
2604:
2602:
2594:
2588:
2585:
2583:
2580:
2578:
2575:
2573:
2570:
2568:
2565:
2563:
2560:
2558:
2555:
2553:
2550:
2549:
2547:
2545:
2539:
2533:
2530:
2528:
2525:
2523:
2520:
2519:
2517:
2515:
2511:
2505:
2502:
2500:
2497:
2495:
2492:
2490:
2487:
2485:
2482:
2480:
2477:
2475:
2472:
2470:
2467:
2466:
2464:
2462:
2461:Amyl alcohols
2458:
2443:
2440:
2433:
2429:
2426:
2419:
2416:
2409:
2405:
2402:
2395:
2391:
2388:
2381:
2378:
2376:
2373:
2372:
2370:
2368:
2364:
2358:
2355:
2354:
2352:
2348:
2342:
2339:
2337:
2334:
2333:
2331:
2327:
2316:
2315:Cetyl alcohol
2313:
2306:
2303:
2296:
2293:
2286:
2283:
2276:
2273:
2266:
2263:
2262:
2260:
2256:
2253:
2249:
2243:
2240:
2238:
2235:
2233:
2231:
2227:
2225:
2224:-Amyl alcohol
2223:
2219:
2217:
2215:
2210:
2208:
2205:
2203:
2202:Ethchlorvynol
2200:
2198:
2195:
2193:
2190:
2188:
2185:
2183:
2180:
2178:
2175:
2173:
2170:
2169:
2167:
2165:alcohols (3°)
2161:
2156:
2153:
2151:
2148:
2146:
2143:
2141:
2138:
2136:
2133:
2131:
2130:Cyclopropanol
2128:
2126:
2125:Cyclopentanol
2123:
2121:
2118:
2116:
2113:
2111:
2108:
2106:
2103:
2101:
2098:
2096:
2093:
2091:
2088:
2086:
2083:
2081:
2078:
2076:
2073:
2071:
2068:
2066:
2063:
2061:
2058:
2056:
2054:alcohols (2°)
2050:
2044:
2041:
2039:
2036:
2034:
2031:
2029:
2026:
2024:
2021:
2019:
2016:
2014:
2011:
2009:
2006:
2004:
2001:
1999:
1996:
1994:
1991:
1989:
1986:
1984:
1981:
1979:
1976:
1974:
1971:
1969:
1966:
1964:
1963:Allyl alcohol
1961:
1959:
1956:
1955:
1946:
1943:
1941:
1938:
1936:
1933:
1931:
1928:
1926:
1923:
1921:
1918:
1916:
1913:
1911:
1908:
1906:
1903:
1901:
1898:
1897:
1895:
1880:
1874:
1871:
1869:
1866:
1864:
1861:
1859:
1856:
1854:
1851:
1848:
1845:
1843:
1840:
1837:
1834:
1832:
1829:
1826:
1823:
1822:
1820:
1805:
1799:
1798:1-Nonacosanol
1796:
1793:
1792:1-Octacosanol
1790:
1788:
1785:
1782:
1781:1-Hexacosanol
1779:
1777:
1774:
1771:
1768:
1766:
1763:
1760:
1757:
1755:
1752:
1749:
1746:
1745:
1743:
1728:
1722:
1721:1-Nonadecanol
1719:
1716:
1715:1-Octadecanol
1713:
1711:
1708:
1705:
1704:1-Hexadecanol
1702:
1700:
1697:
1694:
1691:
1689:
1686:
1683:
1680:
1677:
1674:
1671:
1668:
1667:
1665:
1650:
1643:
1640:
1637:
1634:
1632:
1629:
1627:
1624:
1622:
1619:
1617:
1614:
1612:
1609:
1607:
1604:
1602:
1599:
1598:
1596:
1581:
1575:
1573:
1569:
1567:
1564:
1562:
1559:
1558:
1556:
1554:
1550:
1544:
1541:
1539:
1536:
1534:
1532:
1528:
1526:
1524:
1520:
1516:
1514:
1511:
1509:
1506:
1504:
1501:
1499:
1496:
1494:
1491:
1489:
1486:
1484:
1481:
1479:
1476:
1474:
1471:
1469:
1466:
1464:
1461:
1459:
1456:
1454:
1451:
1449:
1446:
1444:
1441:
1439:
1436:
1434:
1431:
1430:
1428:
1426:
1422:
1416:
1413:
1411:
1408:
1406:
1403:
1401:
1398:
1396:
1395:Aminomethanol
1393:
1391:
1388:
1387:
1385:
1383:
1379:
1376:
1373:
1367:
1357:
1354:
1352:
1349:
1348:
1346:
1344:
1340:
1332:
1329:
1328:
1326:
1324:
1321:
1319:
1318:Ethchlorvynol
1316:
1315:
1313:
1311:
1307:
1301:
1298:
1296:
1294:
1290:
1288:
1287:-Amyl alcohol
1286:
1282:
1280:
1277:
1275:
1272:
1270:
1267:
1265:
1262:
1260:
1257:
1255:
1252:
1251:
1249:
1247:
1241:
1238:
1234:
1230:
1223:
1218:
1216:
1211:
1209:
1204:
1203:
1200:
1189:
1185:
1181:
1177:
1170:
1167:
1163:
1159:
1156:
1155:J. Org. Chem.
1150:
1147:
1143:
1139:
1136:
1135:J. Org. Chem.
1129:
1126:
1121:
1119:0-387-35431-X
1115:
1111:
1104:
1101:
1096:
1092:
1088:
1085:
1084:
1076:
1073:
1068:
1064:
1059:
1054:
1050:
1046:
1042:
1039:
1038:
1033:
1026:
1023:
1018:
1014:
1010:
1007:
1006:
1005:J. Org. Chem.
997:
994:
989:
987:0-387-23607-4
983:
979:
975:
971:
964:
961:
956:
952:
948:
945:
944:
936:
933:
928:
927:
922:
915:
912:
907:
906:
898:
895:
890:
886:
881:
876:
872:
868:
865:(7): 1552–5.
864:
860:
856:
849:
846:
841:
837:
833:
829:
825:
821:
817:
810:
807:
802:
798:
794:
790:
783:
780:
776:
772:
768:
762:
759:
755:
751:
748:
747:
740:
737:
732:
728:
724:
720:
713:
710:
705:
703:0-387-23607-4
699:
695:
691:
687:
680:
677:
674:
673:0-435-63120-9
670:
667:. Heinemann.
666:
660:
657:
650:
648:
646:
642:
637:
634:
630:
625:
622:
620:
613:
611:
609:
600:
594:
590:
580:
579:periodic acid
576:
572:
571:sulfuric acid
564:
560:
559:Jones reagent
554:
546:
541:
532:
528:
526:
518:
516:
511:
507:
503:
490:
483:
481:
478:
476:
472:
468:
460:
453:
451:
449:
445:
437:
429:
421:
417:
413:
404:
397:
395:
393:
389:
387:
382:
380:
372:
368:
366:
363:
359:
355:
353:
349:
345:
344:Ley oxidation
339:Niche methods
338:
336:
330:
325:
317:
315:
301:
297:
289:
281:
277:
275:
274:triethylamine
271:
267:
263:
256:
254:
252:
248:
244:
236:
234:
232:
231:sulfuric acid
228:
224:
223:Jones reagent
219:
213:
210:
207:
204:
203:
202:
192:
188:
171:
168:
157:
154:
153:
152:
138:
131:
129:
127:
123:
114:
107:
105:
99:
95:
89:
87:
83:
73:
69:
66:
64:
60:
56:
52:
48:
44:
41:that convert
40:
37:reactions in
36:
32:
19:
5537:Ene reaction
4897:Autoxidation
4866:
4758:Degradation
4649:Azo coupling
4426:Ugi reaction
4026:Ene reaction
3826:Alkynylation
3677:Polyfluorene
3672:Polar effect
3537:Electrophile
3452:Bredt's rule
3422:Baird's rule
3392:Alpha effect
3205:
3143:Substitution
3136:Preparations
3119:
3085:Stigmasterol
3080:β-Sitosterol
2878:Polyglycitol
2868:Maltotriitol
2828:Cyclic sugar
2596:Branched and
2504:Pentan-3-ol
2499:Pentan-2-ol
2494:Pentan-1-ol
2229:
2221:
2213:
2120:Cyclohexanol
1772:(lignoceryl)
1765:1-Tricosanol
1688:1-Tridecanol
1644:(pelargonic)
1571:
1530:
1522:
1518:
1513:Ethanolamine
1292:
1284:
1182:(11): 2091.
1179:
1178:(abstract).
1175:
1169:
1161:
1157:
1154:
1149:
1141:
1137:
1134:
1128:
1109:
1103:
1086:
1083:Angew. Chem.
1081:
1075:
1040:
1035:
1025:
1011:(26): 9658.
1008:
1003:
996:
969:
963:
949:(23): 3027.
946:
941:
935:
924:
914:
903:
897:
862:
858:
848:
823:
819:
809:
792:
788:
782:
774:
770:
766:
761:
753:
749:
744:
739:
722:
718:
712:
685:
679:
664:
659:
638:
626:
623:
617:
604:
556:
539:
514:
487:
479:
464:
409:
390:
383:
376:
356:
342:
334:
285:
260:
240:
220:
217:
186:
184:
142:
119:
97:
93:
90:
78:
67:
30:
29:
4036:Ethenolysis
3682:Ring strain
3652:Nucleophile
3477:Clar's rule
3417:Aromaticity
3201:Protonation
3118:Nonafluoro-
3065:Cholesterol
3042:Trialcohols
2912:Citronellol
2898:Monoterpene
2810:Deoxy sugar
2598:unsaturated
2285:Isopropanol
2212:Nonafluoro-
2140:Isopropanol
1759:1-Docosanol
1750:(arachidyl)
1682:1-Dodecanol
1676:1-Undecanol
1176:Tetrahedron
1089:(9): 1804.
767:Tetrahedron
229:in aqueous
6599:Categories
6320:Ozonolysis
5847:Annulation
5197:Ozonolysis
3316:Topics in
3162:Hydrolysis
3147:haloalkane
3075:Lanosterol
3070:Ergosterol
3006:Dialcohols
2975:Patchoulol
2776:Galactitol
2706:Erythritol
2582:Tridecanol
2404:Erythritol
2305:1-Pentanol
2115:3-Pentanol
2110:2-Pentanol
2080:3-Heptanol
2075:2-Heptanol
2033:Tryptophol
1838:(lacceryl)
1748:1-Icosanol
1695:(myristyl)
1678:(hendecyl)
1631:1-Heptanol
1621:1-Pentanol
1611:1-Propanol
1566:Isobutanol
1300:Tryptophol
1274:Isobutanol
1254:1-Propanol
756:, 7277–87.
651:References
191:pyridinium
176:(pyridine)
162:(pyridine)
147:(pyridine)
86:sulfoxides
5834:reactions
5349:reactions
4844:reactions
4760:reactions
4642:reactions
3784:reactions
3189:Reactions
3171:Hydration
2984:Diterpene
2970:Nerolidol
2960:Bisabolol
2942:Terpineol
2796:Volemitol
2587:Undecanol
2541:Saturated
2442:Volemitol
2295:1-Butanol
2105:2-Octanol
2100:2-Nonanol
2090:3-Hexanol
2085:2-Hexanol
2065:2-Butanol
2052:Secondary
1884:saturated
1809:saturated
1761:(behenyl)
1732:saturated
1717:(stearyl)
1670:1-Decanol
1654:saturated
1642:1-Nonanol
1636:1-Octanol
1626:1-Hexanol
1616:1-Butanol
1585:saturated
840:1463-9270
777:, 2131–35
430:(PhI(OAc)
365:supported
193:cation (C
181:chloride.
47:aldehydes
35:oxidation
3727:Vinylogy
3397:Annulene
3344:Reagents
3275:Category
3049:Glycerol
2986:alcohols
2965:Farnesol
2953:alcohols
2937:Rhodinol
2922:Linalool
2917:Geraniol
2900:alcohols
2858:Lactitol
2853:Maltitol
2837:Inositol
2830:alcohols
2812:alcohols
2766:Sorbitol
2756:Mannitol
2726:Arabitol
2716:Threitol
2696:Glycerol
2432:Sorbitol
2428:Mannitol
2408:Threitol
2390:Glycerol
2357:Glycerol
2265:Methanol
2163:Tertiary
1849:(geddyl)
1684:(lauryl)
1672:(capric)
1638:(capryl)
1601:Methanol
1574:-Butanol
1382:Methanol
1372:alcohols
1356:Methanol
1229:Alcohols
1067:16608311
889:20192259
608:aldehyde
506:pyridine
444:carbonyl
438:(Pb(OAc)
126:benzylic
43:alcohols
3387:A value
3166:epoxide
3058:Sterols
2927:Menthol
2907:Borneol
2863:Isomalt
2819:Fucitol
2746:Xylitol
2736:Ribitol
2577:Octanol
2572:Nonanol
2557:Decanol
2418:Xylitol
2275:Ethanol
1783:(ceryl)
1606:Ethanol
1553:Butanol
1508:Ethanol
1425:Ethanol
1370:Primary
1331:Ethanol
1264:Ethanol
1164:, 2768.
1144:, 9658.
1058:2546575
880:2848477
510:acetone
502:dioxane
465:When a
412:hydroxy
314:NHCl).
122:Allylic
51:ketones
3175:alkene
2993:Phytol
2786:Iditol
2018:Prenol
1116:
1065:
1055:
984:
929:: 920.
908:: 331.
887:
877:
838:
700:
671:
575:esters
519:. KMnO
298:(CO),
201:NH).
59:esters
57:, and
2932:Nerol
725:: 5.
643:uses
629:TEMPO
517:-BuOH
491:(KMnO
434:) or
422:(NaIO
416:diols
346:uses
264:uses
187:salts
3120:tert
2230:tert
2222:tert
2214:tert
1374:(1°)
1293:tert
1285:tert
1158:1992
1138:1999
1114:ISBN
1063:PMID
982:ISBN
885:PMID
836:ISSN
771:2004
750:1991
698:ISBN
669:ISBN
639:The
565:(CrO
294:S),
241:The
124:and
3240:of
3173:of
3164:of
3145:of
2666:— C
1890:— C
1815:— C
1738:— C
1660:— C
1591:— C
1184:doi
1091:doi
1087:120
1053:PMC
1045:doi
1041:128
1013:doi
974:doi
951:doi
875:PMC
867:doi
828:doi
797:doi
754:113
727:doi
690:doi
512:or
426:),
381:.
348:NMO
302:(CO
290:(Me
251:IBX
98:gem
45:to
6601::
2798:(C
2788:(C
2778:(C
2768:(C
2758:(C
2748:(C
2738:(C
2728:(C
2718:(C
2708:(C
2698:(C
2688:(C
2678:(C
2444:(C
2434:(C
2430:,
2420:(C
2410:(C
2406:,
2396:(C
2392:,
2382:(C
2319:16
2317:(C
2307:(C
2297:(C
2287:(C
2277:(C
2267:(C
1892:49
1888:40
1817:39
1813:30
1740:29
1736:20
1662:19
1658:10
1180:37
1162:57
1160:,
1142:64
1140:,
1061:.
1051:.
1034:.
1009:64
980:.
947:30
923:.
883:.
873:.
863:12
861:.
857:.
834:.
824:14
822:.
818:.
793:45
791:.
775:60
773:,
769:,
752:,
723:52
721:.
696:.
647:.
585:IO
581:(H
508:,
504:,
450:.
312:15
276:.
268:,
253:.
233:.
151:.
84:,
53:,
49:,
3309:e
3302:t
3295:v
2802:)
2800:7
2792:)
2790:6
2782:)
2780:6
2772:)
2770:6
2762:)
2760:6
2752:)
2750:5
2742:)
2740:5
2732:)
2730:5
2722:)
2720:4
2712:)
2710:4
2702:)
2700:3
2692:)
2690:2
2682:)
2680:1
2668:7
2664:1
2662:C
2448:)
2446:7
2438:)
2436:6
2424:)
2422:5
2414:)
2412:4
2400:)
2398:3
2386:)
2384:2
2321:)
2311:)
2309:5
2301:)
2299:4
2291:)
2289:3
2281:)
2279:2
2271:)
2269:1
1886:C
1811:C
1734:C
1656:C
1593:9
1589:1
1587:C
1572:n
1531:N
1523:N
1521:,
1519:N
1221:e
1214:t
1207:v
1190:.
1186::
1122:.
1097:.
1093::
1069:.
1047::
1019:.
1015::
990:.
976::
957:.
953::
891:.
869::
842:.
830::
803:.
799::
733:.
729::
706:.
692::
587:6
583:5
567:3
536:4
521:4
515:t
497:4
493:4
440:4
432:2
424:4
310:H
308:6
304:2
292:2
199:5
197:H
195:5
178:2
174:3
164:2
160:3
149:2
145:3
102:2
96:(
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
