220:
699:
608:
674:
685:
161:
705:
Phosphite esters are the least reactive class of reagents used in this reaction. They react to produce phosphonates. They require the most heating for the reaction to occur (120 °C - 160 °C is common). This high temperature allows for fractional distillation to be employed in the removal of
600:
is a competing reaction pathway for α-bromo- and α-chloroketones. Under the reaction conditions a mixture of the Perkow product and the normal
Arbuzov product occur, usually favoring the Perkow product by a significant amount. Using higher temperatures during the reaction can lead to favoring of the
669:
of the reaction. The reaction proceeds smoothly when the R group is aliphatic. When all of A, B and R are aryl groups, a stable phosphonium salt is formed and the reaction proceeds no further under normal conditions. Heating to higher temperatures in the presence of alcohols has been known to give
732:
Phosphinites are the most reactive class of reagents used in this reaction. They react to produce phosphine oxides. They often require very little heating (45 °C) for the reaction to occur and have been known to self-isomerize without the presence of alkyl halides.
259:). These intermediates are occasionally stable enough to be isolated, such as for triaryl phosphites which do not react to form the phosphonate without thermal cleavage of the intermediate (200 °C), or cleavage by alcohols or bases. The displaced
680:
Phosphite salts (Ex: R = Na) can also undergo the reaction with precipitation of the corresponding Na-halide salt. Amidophosphites and silyloxyphosphites have been used before to yield amidophosphonates and phosphinic acids.
504:
664:
groups are known to slow down the rate of the reaction, with electron donating groups increasing the rate of the reaction. This is consistent with initial attack of the phosphorus reagent on the alkyl halide as the
706:
the alkyl halide produced, though excess of the starting alkyl halide can also be used. Solvents are often not used for this reaction, though there is precedent for the improvement of selectivity with its usage.
303:
group initially dissociates from the phosphonium salt followed by attack of the anion. Phosphite esters with tertiary alkyl halide groups can undergo the reaction, which would be unexpected if only an S
4236:
670:
the isomerization product. Cyclic phosphites generally react to eject the non-cyclic OR group, though for some 5-member rings additional heating is required to afford the final cyclic product.
544:
394:
of the anion. There exists many instances of the intermediate phosphonium salts being sufficiently stable that they can be isolated when the anion is weakly nucleophilic, such as with
658:
3352:
3297:
4065:
713:
of the ester to an acid is a common side reaction. The poor availability of substituted phosphonites limits the usage of this class of reagent in the
Arbuzov reaction.
3407:
969:
Jacobsen, H. I.; Griffin, M. J.; Preis, S.; Jensen, E. V. (1957). "Phosphonic Acids. IV. Preparation and
Reactions of β-Ketophosphonate and Enol Phosphate Esters".
3557:
2191:
219:
347:
groups. For example, the triaryl phosphites mentioned above generally do not react because they form stable phosphonium salts. Since aryl groups do not undergo S
4286:
810:
Arbuzov, A. E. (1906). "On the structure of phosphonic acid and its derivates: Isometization and transition of bonds from trivalent to pentavalent phosphorus".
4060:
3162:
1886:
565:
and substituted derivatives have been known to undergo the reaction under photolytic conditions. Secondary alkyl halides often do not react well, producing
2932:
1083:
3732:
1676:
3827:
1931:
3807:
3302:
2469:
2350:
1906:
3897:
3652:
709:
Phosphonites are generally more reactive than phosphite esters. They react to produce phosphinates. Heating is also required for the reaction, but
1119:
2484:
601:
Arbuzov product. The reaction of α-iodoketones give only the
Arbuzov product. Other methods of producing β-ketophosphonates have been developed.
331:
2 reaction is unlikely to be the mechanism for the synthesis of the neopentyl halides in this reaction. Substrates that cannot react through an S
4130:
3587:
4080:
183:. Several reviews have been published. The reaction also occurs for coordinated phosphite ligands, as illustrated by the demethylation of {(C
3692:
3672:
3632:
2439:
4226:
4151:
4035:
2647:
2051:
1382:
4221:
4050:
3707:
3562:
3192:
72:
3037:
2274:
3397:
2887:
2562:
109:
phosphorus species and another alkyl halide. The picture below shows the most common types of substrates undergoing the
Arbuzov reaction;
4301:
4085:
3107:
426:
As a general guideline, the reactivity of the organic halide component can be listed as follows: (from most reactive to least reactive)
3662:
549:
In general, tertiary alkyl halides, aryl halides and vinyl halides do not react. There are notable exceptions to this trend, including
4296:
4010:
3872:
3627:
4186:
3657:
3572:
3542:
3522:
3387:
3382:
2757:
2682:
2325:
2279:
2146:
1407:
4125:
4291:
4251:
4201:
3677:
3427:
3357:
1846:
3887:
3492:
2385:
2106:
3877:
1417:
1055:
1044:
1033:
4045:
3802:
3752:
2542:
2474:
2365:
1941:
1696:
1621:
1402:
604:
The reaction of trivalent phosphorus compounds with alkyl fluorides is abnormal. One example of this reactivity is shown below.
432:
283:
groups experience inversion of configuration at the carbon center attacked by the halide anion. This is what is expected of an S
4385:
3757:
3567:
3042:
2952:
1076:
4331:
4115:
4055:
3457:
3432:
3342:
2922:
2802:
1836:
1332:
4216:
3702:
3497:
1766:
4321:
3907:
3417:
2927:
2872:
2717:
2677:
2509:
2264:
1981:
1831:
752:
4281:
3842:
3797:
3287:
3142:
4316:
4231:
4090:
4005:
3902:
2977:
2632:
2300:
1711:
1272:
4206:
4181:
4166:
3862:
3727:
3682:
3447:
2992:
2842:
2056:
1736:
1681:
4211:
4156:
3687:
3102:
2817:
2812:
2305:
2121:
2111:
1826:
1686:
1636:
1631:
1606:
1512:
4380:
4266:
3867:
3787:
3402:
3367:
3212:
2637:
2597:
2494:
2269:
2021:
1966:
1566:
1277:
1267:
1242:
4241:
3942:
3747:
3182:
2747:
2722:
2662:
2254:
1961:
1611:
1796:
691:
An
Arbuzov type rearrangement can also occur where the O from an OR group acts as the leaving group in the initial S
3532:
3067:
2519:
1741:
1706:
1302:
1237:
1069:
589:
being inert to the reaction conditions. When a halide atom is found in the ester chain off of the phosphorus atom,
65:
4100:
3722:
2782:
2707:
2231:
2066:
1751:
1527:
1487:
1232:
4341:
4246:
3980:
3952:
3922:
3837:
3767:
3697:
3617:
3517:
3477:
3172:
2792:
2091:
2086:
1548:
1412:
515:
320:
4306:
4176:
4040:
3882:
3742:
3262:
2236:
1786:
1746:
1497:
4196:
3792:
3762:
3637:
3592:
3422:
3332:
3147:
3137:
2967:
2524:
2464:
2429:
2216:
2176:
1951:
1821:
1337:
1327:
1257:
3772:
2752:
1776:
1322:
1202:
355:
2 type mechanisms, triaryl phosphites lack a low energy pathway for decomposition of the phosphonium salt. An
3985:
4390:
4276:
4135:
3927:
3852:
3832:
3552:
3502:
3362:
3327:
3267:
3197:
2499:
2479:
2211:
2131:
2026:
1986:
1956:
1891:
1761:
1671:
1661:
1537:
1247:
729:
functional groups cannot be used with phosphonites in the reaction as they all react with the phosphonite.
4015:
3737:
3487:
3467:
3442:
3392:
3307:
3282:
3237:
3207:
3187:
3157:
3122:
3077:
3052:
3027:
2912:
2837:
2617:
2310:
2246:
2046:
1771:
1691:
1377:
1352:
1129:
1124:
4351:
3097:
1721:
57:
3937:
3892:
3607:
3577:
3547:
3482:
3462:
3377:
3372:
3337:
3292:
3277:
3272:
3252:
3242:
3177:
3167:
3047:
2567:
2370:
1946:
1901:
1731:
1467:
1187:
1149:
842:
666:
558:
356:
1397:
1392:
3990:
607:
4120:
4070:
4020:
4000:
3847:
3822:
3537:
3527:
3412:
3227:
3222:
3152:
2937:
2737:
2697:
2627:
2592:
2547:
2514:
2380:
2355:
2335:
2156:
2116:
2076:
2041:
1971:
1726:
1596:
1571:
1109:
661:
582:
383:
698:
4336:
4326:
4311:
3957:
3932:
3917:
3912:
3642:
3597:
3582:
3472:
3452:
3347:
3232:
3217:
3062:
3007:
2997:
2987:
2962:
2727:
2602:
2577:
2489:
2345:
2330:
2315:
2171:
2136:
2081:
1851:
1701:
1646:
1517:
1432:
1292:
1217:
633:
1362:
946:
Gerrard, W.; Green, W. J. (1951). "568. Mechanism of the formation of dialkyl alkylphosphonates".
673:
4075:
4025:
3995:
3857:
3647:
3437:
3322:
3257:
3247:
3012:
2942:
2907:
2902:
2882:
2877:
2822:
2732:
2582:
2444:
2434:
2340:
2126:
2071:
2001:
1921:
1816:
1716:
1651:
1576:
1422:
1287:
1222:
893:
550:
1207:
378:
Stereochemical experiments on cyclic phosphites have revealed the presence of both pentavalent
3812:
3132:
3017:
2982:
2947:
2892:
2847:
2807:
2762:
2742:
2692:
2687:
2657:
2642:
2552:
2459:
2395:
2360:
2186:
2061:
1936:
1861:
1841:
1756:
1591:
1586:
1532:
1442:
1347:
1307:
1262:
1144:
1139:
1104:
1003:
971:
395:
172:
94:
41:
31:
569:
as side-products. Allyl and propargyl halides are also reactive, but can proceed through an S
4346:
4191:
4161:
4105:
4030:
3962:
3717:
3667:
3512:
3317:
3092:
3087:
3032:
3022:
2797:
2607:
2587:
2557:
2454:
2390:
2375:
2206:
2161:
2151:
2141:
2036:
2016:
2011:
1996:
1991:
1871:
1866:
1806:
1791:
1781:
1626:
1616:
1482:
1472:
1462:
1372:
1367:
1342:
1282:
1134:
1093:
979:
951:
928:
883:
875:
792:
742:
684:
252:
168:
27:
4256:
3947:
3782:
3777:
3072:
3057:
3002:
2957:
2917:
2867:
2832:
2827:
2772:
2767:
2702:
2652:
2572:
2400:
2284:
2259:
2221:
2196:
2181:
2166:
2101:
1976:
1926:
1916:
1896:
1856:
1666:
1656:
1641:
1437:
1357:
1182:
1177:
855:
779:"Ueber das Verhalten der Jodalkyle gegen die sogen. Phosphorigsäureester oder O-Phosphine"
747:
722:
597:
391:
180:
175:
soon thereafter. This reaction is widely used for the synthesis of various phosphonates,
150:
110:
1227:
1197:
593:
to the corresponding
Arbuzov product has been known without addition of an alkyl halide.
4261:
4171:
4110:
3202:
3112:
3082:
2857:
2712:
2449:
2226:
2096:
1911:
1881:
1581:
1477:
1252:
1114:
757:
387:
160:
4374:
4271:
3972:
3817:
3712:
3507:
2897:
2862:
2852:
2787:
2777:
2667:
2504:
2320:
2031:
2006:
1876:
1522:
1507:
1492:
1387:
1317:
1297:
1212:
714:
590:
244:
897:
3312:
2672:
2424:
2201:
1801:
1601:
1452:
1447:
1312:
1167:
630:
The general form of the trivalent phosphorus reagent can be considered as follows:
292:
236:
228:
208:
102:
1811:
1457:
1427:
1192:
998:
918:
Bhattacharya, A. K.; Thyagarajan, G. (1981). "Michaelis–Arbuzov rearrangement".
578:
562:
379:
368:
340:
311:
1 type mechanism comes from the use of the
Arbuzov reaction in the synthesis of
288:
176:
142:
134:
126:
118:
106:
4095:
3622:
2972:
1061:
920:
796:
586:
695:
2 attack of the phosphorus. This is only known to occur when A and B are Cl.
888:
870:
710:
372:
312:
98:
1502:
1172:
955:
783:
399:
983:
932:
1162:
315:
halides, a class of compounds that are notoriously unreactive towards S
390:. The decomposition of these intermediates is driven primarily by the
585:
interestingly enough, only undergoes the reaction a single time with
566:
554:
271:
carbons, displacing the oxygen atom to give the desired phosphonate (
260:
778:
1054:, Coll. Vol. 10, p. 289 (2004); Vol. 78, p. 169 (2002). (
1043:, Coll. Vol. 8, p. 451 (1993); Vol. 65, p. 119 (1987). (
726:
718:
1032:, Coll. Vol. 4, p. 325 (1963); Vol. 31, p. 33 (1951). (
344:
1546:
1065:
660:
with A and B generally being alkyl, alkoxy or aryloxy groups.
386:
being involved in the dealkylation step of the reaction using
697:
683:
672:
606:
218:
159:
499:{\displaystyle {\ce {RCOX>RCH2X>RR'CHX\gg RR'R''CX}}}
279:). This has been supported by the observation that chiral R
453:
323:, the inert nature of the neopentyl halides towards the S
577:
2` mechanism. Reaction with primary alkyl halides and
557:
halides. Some activated aryl halides, often involving
636:
518:
435:
307:
2 mechanism was operating. Further support for this S
227:
The
Michaelis–Arbuzov reaction is initiated with the
4237:
Erlenmeyer–Plöchl azlactone and amino-acid synthesis
4144:
3971:
3606:
3121:
2616:
2533:
2413:
2293:
2245:
1555:
652:
538:
498:
3298:Divinylcyclopropane-cycloheptadiene rearrangement
997:Nagata, W.; Wakabayashi, T.; Hayase, Y. (1988).
339:1 pathway generally do not react, which include
1039:Davidsen, S. K.; Phllips, G. W.; Martin, S. F.
223:The mechanism of the Michaelis–Arbuzov reaction
3558:Thermal rearrangement of aromatic hydrocarbons
2192:Thermal rearrangement of aromatic hydrocarbons
291:based mechanism of dealkylation similar to an
4287:Lectka enantioselective beta-lactam synthesis
1077:
999:"Diethyl 2-(cyclohexylamino)vinylphosphonate"
382:and tetravalent phosphonium intermediates in
8:
4066:Inverse electron-demand Diels–Alder reaction
1887:Heterogeneous metal catalyzed cross-coupling
539:{\displaystyle {\ce {RI > RBr > RCl}}}
3408:Lobry de Bruyn–Van Ekenstein transformation
3968:
2242:
1543:
1084:
1070:
1062:
871:"Michaelis–Arbusow- und Perkow-Reaktionen"
15:
3898:Petrenko-Kritschenko piperidone synthesis
3353:Fritsch–Buttenberg–Wiechell rearrangement
887:
641:
637:
635:
561:have been known to undergo the reaction.
519:
517:
452:
447:
436:
434:
4061:Intramolecular Diels–Alder cycloaddition
1050:Enders, D.; von Berg, S.; Jandeleit, B.
769:
319:2 reactions. Based on the principle of
287:2 reaction. Evidence also exists for a
263:anion then usually reacts via another S
4081:Metal-centered cycloaddition reactions
3733:Debus–Radziszewski imidazole synthesis
1677:Bodroux–Chichibabin aldehyde synthesis
851:
840:
4227:Diazoalkane 1,3-dipolar cycloaddition
4131:Vinylcyclopropane (5+2) cycloaddition
4036:Diazoalkane 1,3-dipolar cycloaddition
3808:Hurd–Mori 1,2,3-thiadiazole synthesis
3303:Dowd–Beckwith ring-expansion reaction
2470:Hurd–Mori 1,2,3-thiadiazole synthesis
1383:LFER solvent coefficients (data page)
7:
3038:Sharpless asymmetric dihydroxylation
2275:Methoxymethylenetriphenylphosphorane
913:
911:
909:
907:
3163:Allen–Millar–Trippett rearrangement
4302:Nitrone-olefin (3+2) cycloaddition
4297:Niementowski quinazoline synthesis
4086:Nitrone-olefin (3+2) cycloaddition
4011:Azide-alkyne Huisgen cycloaddition
3873:Niementowski quinazoline synthesis
3628:Azide-alkyne Huisgen cycloaddition
2933:Meerwein–Ponndorf–Verley reduction
2485:Leimgruber–Batcho indole synthesis
777:Michaelis, A.; Kaehne, R. (1898).
14:
4126:Trimethylenemethane cycloaddition
3828:Johnson–Corey–Chaykovsky reaction
3693:Cadogan–Sundberg indole synthesis
3673:Bohlmann–Rahtz pyridine synthesis
3633:Baeyer–Emmerling indole synthesis
2440:Cadogan–Sundberg indole synthesis
1932:Johnson–Corey–Chaykovsky reaction
171:in 1898, and greatly explored by
4222:Cook–Heilbron thiazole synthesis
4051:Hexadehydro Diels–Alder reaction
3878:Niementowski quinoline synthesis
3708:Cook–Heilbron thiazole synthesis
3653:Bischler–Möhlau indole synthesis
3563:Tiffeneau–Demjanov rearrangement
3193:Baker–Venkataraman rearrangement
2351:Horner–Wadsworth–Emmons reaction
2022:Mizoroki-Heck vs. Reductive Heck
1907:Horner–Wadsworth–Emmons reaction
1418:Neighbouring group participation
1028:Ford-Moore, A. H.; Perry, B. J.
3758:Fiesselmann thiophene synthesis
3588:Westphalen–Lettré rearrangement
3568:Vinylcyclopropane rearrangement
3398:Kornblum–DeLaMare rearrangement
3043:Epoxidation of allylic alcohols
2953:Noyori asymmetric hydrogenation
2888:Kornblum–DeLaMare rearrangement
2563:Gallagher–Hollander degradation
167:The reaction was discovered by
4217:Chichibabin pyridine synthesis
3703:Chichibabin pyridine synthesis
3663:Blum–Ittah aziridine synthesis
3498:Ring expansion and contraction
1767:Cross dehydrogenative coupling
653:{\displaystyle {\ce {ABP-OR}}}
367:) has also been implicated in
327:2 reaction indicates that an S
1:
4187:Bischler–Napieralski reaction
4145:Heterocycle forming reactions
3798:Hemetsberger indole synthesis
3658:Bischler–Napieralski reaction
3573:Wagner–Meerwein rearrangement
3543:Sommelet–Hauser rearrangement
3523:Seyferth–Gilbert homologation
3388:Ireland–Claisen rearrangement
3383:Hofmann–Martius rearrangement
3143:2,3-sigmatropic rearrangement
2758:Corey–Winter olefin synthesis
2683:Barton–McCombie deoxygenation
2326:Corey–Winter olefin synthesis
2280:Seyferth–Gilbert homologation
2147:Seyferth–Gilbert homologation
4292:Lehmstedt–Tanasescu reaction
4252:Gabriel–Colman rearrangement
4207:Bucherer carbazole synthesis
4202:Borsche–Drechsel cyclization
4182:Bernthsen acridine synthesis
4167:Bamberger triazine synthesis
4152:Algar–Flynn–Oyamada reaction
3863:Nazarov cyclization reaction
3728:De Kimpe aziridine synthesis
3683:Bucherer carbazole synthesis
3678:Borsche–Drechsel cyclization
3448:Nazarov cyclization reaction
3428:Meyer–Schuster rearrangement
3358:Gabriel–Colman rearrangement
3108:Wolffenstein–Böters reaction
2993:Reduction of nitro compounds
2843:Grundmann aldehyde synthesis
2648:Algar–Flynn–Oyamada reaction
2057:Olefin conversion technology
2052:Nozaki–Hiyama–Kishi reaction
1847:Gabriel–Colman rearrangement
1737:Claisen-Schmidt condensation
1682:Bouveault aldehyde synthesis
581:generally proceed smoothly.
275:) and another alkyl halide (
4267:Hantzsch pyridine synthesis
4046:Enone–alkene cycloadditions
3868:Nenitzescu indole synthesis
3788:Hantzsch pyridine synthesis
3753:Ferrario–Ackermann reaction
3403:Kowalski ester homologation
3368:Halogen dance rearrangement
3213:Benzilic acid rearrangement
2638:Akabori amino-acid reaction
2598:Von Braun amide degradation
2543:Barbier–Wieland degradation
2495:Nenitzescu indole synthesis
2475:Kharasch–Sosnovsky reaction
2366:Julia–Kocienski olefination
2270:Kowalski ester homologation
1967:Kowalski ester homologation
1942:Julia–Kocienski olefination
1697:Cadiot–Chodkiewicz coupling
1622:Aza-Baylis–Hillman reaction
1567:Acetoacetic ester synthesis
1278:Dynamic binding (chemistry)
1268:Conrotatory and disrotatory
1243:Charge remote fragmentation
19:Michaelis–Arbuzov reaction
4407:
4332:Robinson–Gabriel synthesis
4282:Kröhnke pyridine synthesis
4116:Retro-Diels–Alder reaction
4056:Imine Diels–Alder reaction
3843:Kröhnke pyridine synthesis
3458:Newman–Kwart rearrangement
3433:Mislow–Evans rearrangement
3343:Fischer–Hepp rearrangement
3288:Di-π-methane rearrangement
3068:Stephen aldehyde synthesis
2803:Eschweiler–Clarke reaction
2520:Williamson ether synthesis
1837:Fujiwara–Moritani reaction
1742:Combes quinoline synthesis
1707:Carbonyl olefin metathesis
1408:More O'Ferrall–Jencks plot
1333:Grunwald–Winstein equation
1303:Electron-withdrawing group
1238:Catalytic resonance theory
1013:, vol. 6, p. 448
267:2 reaction on one of the R
87:Michaelis–Arbuzov reaction
4342:Urech hydantoin synthesis
4322:Pomeranz–Fritsch reaction
4247:Fischer oxazole synthesis
3981:1,3-Dipolar cycloaddition
3953:Urech hydantoin synthesis
3923:Reissert indole synthesis
3908:Pomeranz–Fritsch reaction
3838:Knorr quinoline synthesis
3768:Fischer oxazole synthesis
3698:Camps quinoline synthesis
3618:1,3-Dipolar cycloaddition
3518:Semipinacol rearrangement
3493:Ramberg–Bäcklund reaction
3478:Piancatelli rearrangement
3418:McFadyen–Stevens reaction
3173:Alpha-ketol rearrangement
2928:McFadyen–Stevens reaction
2873:Kiliani–Fischer synthesis
2793:Elbs persulfate oxidation
2718:Bouveault–Blanc reduction
2678:Baeyer–Villiger oxidation
2510:Schotten–Baumann reaction
2386:Ramberg–Bäcklund reaction
2265:Kiliani–Fischer synthesis
2107:Ramberg–Bäcklund reaction
2092:Pinacol coupling reaction
2087:Piancatelli rearrangement
1982:Liebeskind–Srogl coupling
1832:Fujimoto–Belleau reaction
1549:List of organic reactions
1413:Negative hyperconjugation
1158:
1100:
797:10.1002/cber.189803101190
753:Michaelis–Becker reaction
321:microscopic reversibility
101:phosphorus ester with an
79:
53:Organic Chemistry Portal
47:
18:
4317:Pictet–Spengler reaction
4232:Einhorn–Brunner reaction
4197:Boger pyridine synthesis
4091:Oxo-Diels–Alder reaction
4006:Aza-Diels–Alder reaction
3903:Pictet–Spengler reaction
3803:Hofmann–Löffler reaction
3793:Hegedus indole synthesis
3763:Fischer indole synthesis
3638:Bartoli indole synthesis
3593:Willgerodt rearrangement
3423:McLafferty rearrangement
3333:Ferrier carbocyclization
3148:2,3-Wittig rearrangement
3138:1,2-Wittig rearrangement
2978:Parikh–Doering oxidation
2968:Oxygen rebound mechanism
2633:Adkins–Peterson reaction
2525:Yamaguchi esterification
2465:Hegedus indole synthesis
2430:Bartoli indole synthesis
2301:Bamford–Stevens reaction
2217:Weinreb ketone synthesis
2177:Stork enamine alkylation
1952:Knoevenagel condensation
1822:Ferrier carbocyclization
1712:Castro–Stephens coupling
1338:Hammett acidity function
1328:Free-energy relationship
1273:Curtin–Hammett principle
1258:Conformational isomerism
812:J. Russ. Phys. Chem. Soc
725:, primary and secondary
243:- A phosphite) with the
4277:Knorr pyrrole synthesis
4212:Bucherer–Bergs reaction
4157:Allan–Robinson reaction
4136:Wagner-Jauregg reaction
3928:Ring-closing metathesis
3853:Larock indole synthesis
3833:Knorr pyrrole synthesis
3688:Bucherer–Bergs reaction
3553:Stieglitz rearrangement
3533:Skattebøl rearrangement
3503:Ring-closing metathesis
3363:Group transfer reaction
3328:Favorskii rearrangement
3268:Cornforth rearrangement
3198:Bamberger rearrangement
3103:Wolff–Kishner reduction
2923:Markó–Lam deoxygenation
2818:Fleming–Tamao oxidation
2813:Fischer–Tropsch process
2500:Oxymercuration reaction
2480:Knorr pyrrole synthesis
2306:Barton–Kellogg reaction
2212:Wagner-Jauregg reaction
2132:Ring-closing metathesis
2122:Reimer–Tiemann reaction
2112:Rauhut–Currier reaction
2027:Nef isocyanide reaction
1987:Malonic ester synthesis
1957:Knorr pyrrole synthesis
1892:High dilution principle
1827:Friedel–Crafts reaction
1762:Cross-coupling reaction
1687:Bucherer–Bergs reaction
1672:Blanc chloromethylation
1662:Blaise ketone synthesis
1637:Baylis–Hillman reaction
1632:Barton–Kellogg reaction
1607:Allan–Robinson reaction
1513:Woodward–Hoffmann rules
1248:Charge-transfer complex
889:10.1351/pac196409020307
869:Arbuzov, B. A. (1964).
829:Arbuzov, A. E. (1906).
207:}, which is called the
4386:Substitution reactions
4242:Feist–Benary synthesis
4016:Bradsher cycloaddition
3986:4+4 Photocycloaddition
3943:Simmons–Smith reaction
3888:Paternò–Büchi reaction
3748:Feist–Benary synthesis
3738:Dieckmann condensation
3488:Pummerer rearrangement
3468:Oxy-Cope rearrangement
3443:Myers allene synthesis
3393:Jacobsen rearrangement
3308:Electrocyclic reaction
3283:Demjanov rearrangement
3238:Buchner ring expansion
3208:Beckmann rearrangement
3188:Aza-Cope rearrangement
3183:Arndt–Eistert reaction
3158:Alkyne zipper reaction
3078:Transfer hydrogenation
3053:Sharpless oxyamination
3028:Selenoxide elimination
2913:Lombardo methylenation
2838:Griesbaum coozonolysis
2748:Corey–Itsuno reduction
2723:Boyland–Sims oxidation
2663:Angeli–Rimini reaction
2311:Boord olefin synthesis
2255:Arndt–Eistert reaction
2247:Homologation reactions
2047:Nitro-Mannich reaction
1962:Kolbe–Schmitt reaction
1772:Cross-coupling partner
1692:Buchner ring expansion
1612:Arndt–Eistert reaction
1378:Kinetic isotope effect
1125:Rearrangement reaction
702:
688:
677:
654:
611:
540:
500:
224:
164:
4101:Pauson–Khand reaction
3938:Sharpless epoxidation
3893:Pechmann condensation
3773:Friedländer synthesis
3723:Davis–Beirut reaction
3578:Wallach rearrangement
3548:Stevens rearrangement
3483:Pinacol rearrangement
3463:Overman rearrangement
3378:Hofmann rearrangement
3373:Hayashi rearrangement
3338:Ferrier rearrangement
3293:Dimroth rearrangement
3278:Curtius rearrangement
3273:Criegee rearrangement
3253:Claisen rearrangement
3243:Carroll rearrangement
3178:Amadori rearrangement
3168:Allylic rearrangement
3048:Sharpless epoxidation
2783:Dess–Martin oxidation
2708:Bohn–Schmidt reaction
2568:Hofmann rearrangement
2371:Kauffmann olefination
2294:Olefination reactions
2232:Wurtz–Fittig reaction
2067:Palladium–NHC complex
1947:Kauffmann olefination
1902:Homologation reaction
1752:Corey–House synthesis
1732:Claisen rearrangement
1528:Yukawa–Tsuno equation
1488:Swain–Lupton equation
1468:Spherical aromaticity
1403:Möbius–Hückel concept
1188:Aromatic ring current
1150:Substitution reaction
701:
687:
676:
667:rate-determining step
655:
610:
541:
501:
357:allylic rearrangement
222:
163:
4307:Paal–Knorr synthesis
4177:Barton–Zard reaction
4121:Staudinger synthesis
4071:Ketene cycloaddition
4041:Diels–Alder reaction
4021:Cheletropic reaction
4001:Alkyne trimerisation
3883:Paal–Knorr synthesis
3848:Kulinkovich reaction
3823:Jacobsen epoxidation
3743:Diels–Alder reaction
3538:Smiles rearrangement
3528:Sigmatropic reaction
3413:Lossen rearrangement
3263:Corey–Fuchs reaction
3228:Boekelheide reaction
3223:Bergmann degradation
3153:Achmatowicz reaction
2938:Methionine sulfoxide
2738:Clemmensen reduction
2698:Bergmann degradation
2628:Acyloin condensation
2593:Strecker degradation
2548:Bergmann degradation
2515:Ullmann condensation
2381:Peterson olefination
2356:Hydrazone iodination
2336:Elimination reaction
2237:Zincke–Suhl reaction
2157:Sonogashira coupling
2117:Reformatsky reaction
2077:Peterson olefination
2042:Nierenstein reaction
1972:Kulinkovich reaction
1787:Diels–Alder reaction
1747:Corey–Fuchs reaction
1727:Claisen condensation
1597:Alkyne trimerisation
1572:Acyloin condensation
1538:Σ-bishomoaromaticity
1498:Thorpe–Ingold effect
1110:Elimination reaction
956:10.1039/jr9510002550
662:Electron-withdrawing
634:
583:Carbon tetrachloride
516:
433:
384:chemical equilibrium
255:as an intermediate (
239:phosphorus species (
4327:Prilezhaev reaction
4312:Pellizzari reaction
3991:(4+3) cycloaddition
3958:Van Leusen reaction
3933:Robinson annulation
3918:Pschorr cyclization
3913:Prilezhaev reaction
3643:Bergman cyclization
3598:Wolff rearrangement
3583:Weerman degradation
3473:Pericyclic reaction
3453:Neber rearrangement
3348:Fries rearrangement
3233:Brook rearrangement
3218:Bergman cyclization
3063:Staudinger reaction
3008:Rosenmund reduction
2998:Reductive amination
2963:Oppenauer oxidation
2753:Corey–Kim oxidation
2728:Cannizzaro reaction
2603:Weerman degradation
2578:Isosaccharinic acid
2490:Mukaiyama hydration
2346:Hofmann elimination
2331:Dehydrohalogenation
2316:Chugaev elimination
2137:Robinson annulation
2082:Pfitzinger reaction
1852:Gattermann reaction
1797:Wulff–Dötz reaction
1777:Dakin–West reaction
1702:Carbonyl allylation
1647:Bergman cyclization
1433:Kennedy J. P. Orton
1353:Hammond's postulate
1323:Flippin–Lodge angle
1293:Electromeric effect
1218:Beta-silicon effect
1203:Baker–Nathan effect
984:10.1021/ja01567a067
933:10.1021/cr00044a004
615:Phosphorus reactant
455:
4381:Coupling reactions
4076:McCormack reaction
4026:Conia-ene reaction
3858:Madelung synthesis
3648:Biginelli reaction
3438:Mumm rearrangement
3323:Favorskii reaction
3258:Cope rearrangement
3248:Chan rearrangement
3013:Rubottom oxidation
2943:Miyaura borylation
2908:Lipid peroxidation
2903:Lindgren oxidation
2883:Kornblum oxidation
2878:Kolbe electrolysis
2823:Fukuyama reduction
2733:Carbonyl reduction
2583:Marker degradation
2445:Diazonium compound
2435:Boudouard reaction
2414:Carbon-heteroatom
2341:Grieco elimination
2127:Rieche formylation
2072:Passerini reaction
2002:Meerwein arylation
1922:Hydroxymethylation
1817:Favorskii reaction
1717:Chan rearrangement
1652:Biginelli reaction
1577:Aldol condensation
1423:2-Norbornyl cation
1398:Möbius aromaticity
1393:Markovnikov's rule
1288:Effective molarity
1233:Bürgi–Dunitz angle
1223:Bicycloaromaticity
703:
689:
678:
650:
612:
551:1,2-dichloroethene
536:
496:
443:
225:
215:Reaction mechanism
165:
4368:
4367:
4364:
4363:
4360:
4359:
4352:Wohl–Aue reaction
3996:6+4 Cycloaddition
3813:Iodolactonization
3133:1,2-rearrangement
3098:Wohl–Aue reaction
3018:Sabatier reaction
2983:Pinnick oxidation
2948:Mozingo reduction
2893:Leuckart reaction
2848:Haloform reaction
2763:Criegee oxidation
2743:Collins oxidation
2693:Benkeser reaction
2688:Bechamp reduction
2658:Andrussow process
2643:Alcohol oxidation
2553:Edman degradation
2460:Haloform reaction
2409:
2408:
2396:Takai olefination
2361:Julia olefination
2187:Takai olefination
2062:Olefin metathesis
1937:Julia olefination
1862:Grignard reaction
1842:Fukuyama coupling
1757:Coupling reaction
1722:Chan–Lam coupling
1592:Alkyne metathesis
1587:Alkane metathesis
1443:Phosphaethynolate
1348:George S. Hammond
1308:Electronic effect
1263:Conjugated system
1145:Stereospecificity
1140:Stereoselectivity
1105:Addition reaction
1094:organic reactions
1052:Organic Syntheses
1041:Organic Syntheses
1030:Organic Syntheses
1011:Collected Volumes
1004:Organic Syntheses
972:J. Am. Chem. Soc.
850:Missing or empty
648:
640:
534:
528:
522:
494:
487:
479:
472:
465:
458:
446:
439:
396:tetrafluoroborate
335:2 pathway or an S
173:Aleksandr Arbuzov
95:chemical reaction
89:(also called the
83:
82:
42:Coupling reaction
32:Aleksandr Arbuzov
4398:
4347:Wenker synthesis
4337:Stollé synthesis
4192:Bobbitt reaction
4162:Auwers synthesis
4106:Povarov reaction
4031:Cyclopropanation
3969:
3963:Wenker synthesis
3718:Darzens reaction
3668:Bobbitt reaction
3513:Schmidt reaction
3318:Enyne metathesis
3093:Whiting reaction
3088:Wharton reaction
3033:Shapiro reaction
3023:Sarett oxidation
2988:Prévost reaction
2798:Emde degradation
2608:Wohl degradation
2588:Ruff degradation
2558:Emde degradation
2455:Grignard reagent
2391:Shapiro reaction
2376:McMurry reaction
2243:
2207:Ullmann reaction
2172:Stollé synthesis
2162:Stetter reaction
2152:Shapiro reaction
2142:Sakurai reaction
2037:Negishi coupling
2017:Minisci reaction
2012:Michael reaction
1997:McMurry reaction
1992:Mannich reaction
1872:Hammick reaction
1867:Grignard reagent
1807:Enyne metathesis
1792:Doebner reaction
1782:Darzens reaction
1627:Barbier reaction
1617:Auwers synthesis
1544:
1518:Woodward's rules
1483:Superaromaticity
1473:Spiroaromaticity
1373:Inductive effect
1368:Hyperconjugation
1343:Hammett equation
1283:Edwards equation
1135:Regioselectivity
1086:
1079:
1072:
1063:
1016:
1014:
1007:
994:
988:
987:
966:
960:
959:
943:
937:
936:
915:
902:
901:
891:
876:Pure Appl. Chem.
866:
860:
859:
853:
848:
846:
838:
826:
820:
819:
807:
801:
800:
774:
743:Abramov reaction
659:
657:
656:
651:
649:
646:
645:
638:
627:
626:
622:
545:
543:
542:
537:
535:
532:
526:
520:
505:
503:
502:
497:
495:
492:
491:
485:
483:
477:
470:
469:
463:
456:
454:
451:
444:
437:
423:
422:
418:
253:phosphonium salt
181:phosphine oxides
169:August Michaelis
151:phosphine oxides
149:) react to form
133:) react to form
117:) react to form
111:phosphite esters
91:Arbuzov reaction
75:
60:
58:arbuzov-reaction
28:August Michaelis
16:
4406:
4405:
4401:
4400:
4399:
4397:
4396:
4395:
4371:
4370:
4369:
4356:
4257:Gewald reaction
4140:
3967:
3948:Skraup reaction
3783:Graham reaction
3778:Gewald reaction
3609:
3602:
3124:
3117:
3073:Swern oxidation
3058:Stahl oxidation
3003:Riley oxidation
2958:Omega oxidation
2918:Luche reduction
2868:Jones oxidation
2833:Glycol cleavage
2828:Ganem oxidation
2773:Davis oxidation
2768:Dakin oxidation
2703:Birch reduction
2653:Amide reduction
2619:
2612:
2573:Hooker reaction
2535:
2529:
2417:
2415:
2405:
2401:Wittig reaction
2289:
2285:Wittig reaction
2260:Hooker reaction
2241:
2222:Wittig reaction
2197:Thorpe reaction
2182:Suzuki reaction
2167:Stille reaction
2102:Quelet reaction
1977:Kumada coupling
1927:Ivanov reaction
1917:Hydrovinylation
1897:Hiyama coupling
1857:Glaser coupling
1667:Blaise reaction
1657:Bingel reaction
1642:Benary reaction
1559:
1557:
1551:
1542:
1438:Passive binding
1358:Homoaromaticity
1208:Baldwin's rules
1183:Antiaromaticity
1178:Anomeric effect
1154:
1096:
1090:
1025:
1020:
1019:
1009:
996:
995:
991:
968:
967:
963:
945:
944:
940:
917:
916:
905:
868:
867:
863:
849:
839:
828:
827:
823:
809:
808:
804:
776:
775:
771:
766:
748:Perkow reaction
739:
723:carboxylic acid
694:
632:
631:
628:
624:
620:
618:
617:
598:Perkow reaction
576:
572:
514:
513:
484:
476:
462:
431:
430:
424:
420:
416:
414:
413:
408:
392:nucleophilicity
364:
354:
350:
338:
334:
330:
326:
318:
310:
306:
302:
296:
286:
282:
270:
266:
232:
217:
206:
202:
198:
194:
190:
186:
71:
56:
30:
12:
11:
5:
4404:
4402:
4394:
4393:
4391:Name reactions
4388:
4383:
4373:
4372:
4366:
4365:
4362:
4361:
4358:
4357:
4355:
4354:
4349:
4344:
4339:
4334:
4329:
4324:
4319:
4314:
4309:
4304:
4299:
4294:
4289:
4284:
4279:
4274:
4269:
4264:
4262:Hantzsch ester
4259:
4254:
4249:
4244:
4239:
4234:
4229:
4224:
4219:
4214:
4209:
4204:
4199:
4194:
4189:
4184:
4179:
4174:
4172:Banert cascade
4169:
4164:
4159:
4154:
4148:
4146:
4142:
4141:
4139:
4138:
4133:
4128:
4123:
4118:
4113:
4111:Prato reaction
4108:
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:
3977:
3975:
3966:
3965:
3960:
3955:
3950:
3945:
3940:
3935:
3930:
3925:
3920:
3915:
3910:
3905:
3900:
3895:
3890:
3885:
3880:
3875:
3870:
3865:
3860:
3855:
3850:
3845:
3840:
3835:
3830:
3825:
3820:
3815:
3810:
3805:
3800:
3795:
3790:
3785:
3780:
3775:
3770:
3765:
3760:
3755:
3750:
3745:
3740:
3735:
3730:
3725:
3720:
3715:
3710:
3705:
3700:
3695:
3690:
3685:
3680:
3675:
3670:
3665:
3660:
3655:
3650:
3645:
3640:
3635:
3630:
3625:
3620:
3614:
3612:
3604:
3603:
3601:
3600:
3595:
3590:
3585:
3580:
3575:
3570:
3565:
3560:
3555:
3550:
3545:
3540:
3535:
3530:
3525:
3520:
3515:
3510:
3505:
3500:
3495:
3490:
3485:
3480:
3475:
3470:
3465:
3460:
3455:
3450:
3445:
3440:
3435:
3430:
3425:
3420:
3415:
3410:
3405:
3400:
3395:
3390:
3385:
3380:
3375:
3370:
3365:
3360:
3355:
3350:
3345:
3340:
3335:
3330:
3325:
3320:
3315:
3310:
3305:
3300:
3295:
3290:
3285:
3280:
3275:
3270:
3265:
3260:
3255:
3250:
3245:
3240:
3235:
3230:
3225:
3220:
3215:
3210:
3205:
3203:Banert cascade
3200:
3195:
3190:
3185:
3180:
3175:
3170:
3165:
3160:
3155:
3150:
3145:
3140:
3135:
3129:
3127:
3123:Rearrangement
3119:
3118:
3116:
3115:
3113:Zinin reaction
3110:
3105:
3100:
3095:
3090:
3085:
3083:Wacker process
3080:
3075:
3070:
3065:
3060:
3055:
3050:
3045:
3040:
3035:
3030:
3025:
3020:
3015:
3010:
3005:
3000:
2995:
2990:
2985:
2980:
2975:
2970:
2965:
2960:
2955:
2950:
2945:
2940:
2935:
2930:
2925:
2920:
2915:
2910:
2905:
2900:
2895:
2890:
2885:
2880:
2875:
2870:
2865:
2860:
2858:Hydrogenolysis
2855:
2850:
2845:
2840:
2835:
2830:
2825:
2820:
2815:
2810:
2808:Étard reaction
2805:
2800:
2795:
2790:
2785:
2780:
2775:
2770:
2765:
2760:
2755:
2750:
2745:
2740:
2735:
2730:
2725:
2720:
2715:
2713:Bosch reaction
2710:
2705:
2700:
2695:
2690:
2685:
2680:
2675:
2670:
2665:
2660:
2655:
2650:
2645:
2640:
2635:
2630:
2624:
2622:
2618:Organic redox
2614:
2613:
2611:
2610:
2605:
2600:
2595:
2590:
2585:
2580:
2575:
2570:
2565:
2560:
2555:
2550:
2545:
2539:
2537:
2531:
2530:
2528:
2527:
2522:
2517:
2512:
2507:
2502:
2497:
2492:
2487:
2482:
2477:
2472:
2467:
2462:
2457:
2452:
2450:Esterification
2447:
2442:
2437:
2432:
2427:
2421:
2419:
2411:
2410:
2407:
2406:
2404:
2403:
2398:
2393:
2388:
2383:
2378:
2373:
2368:
2363:
2358:
2353:
2348:
2343:
2338:
2333:
2328:
2323:
2318:
2313:
2308:
2303:
2297:
2295:
2291:
2290:
2288:
2287:
2282:
2277:
2272:
2267:
2262:
2257:
2251:
2249:
2240:
2239:
2234:
2229:
2227:Wurtz reaction
2224:
2219:
2214:
2209:
2204:
2199:
2194:
2189:
2184:
2179:
2174:
2169:
2164:
2159:
2154:
2149:
2144:
2139:
2134:
2129:
2124:
2119:
2114:
2109:
2104:
2099:
2097:Prins reaction
2094:
2089:
2084:
2079:
2074:
2069:
2064:
2059:
2054:
2049:
2044:
2039:
2034:
2029:
2024:
2019:
2014:
2009:
2004:
1999:
1994:
1989:
1984:
1979:
1974:
1969:
1964:
1959:
1954:
1949:
1944:
1939:
1934:
1929:
1924:
1919:
1914:
1912:Hydrocyanation
1909:
1904:
1899:
1894:
1889:
1884:
1882:Henry reaction
1879:
1874:
1869:
1864:
1859:
1854:
1849:
1844:
1839:
1834:
1829:
1824:
1819:
1814:
1809:
1804:
1799:
1794:
1789:
1784:
1779:
1774:
1769:
1764:
1759:
1754:
1749:
1744:
1739:
1734:
1729:
1724:
1719:
1714:
1709:
1704:
1699:
1694:
1689:
1684:
1679:
1674:
1669:
1664:
1659:
1654:
1649:
1644:
1639:
1634:
1629:
1624:
1619:
1614:
1609:
1604:
1599:
1594:
1589:
1584:
1582:Aldol reaction
1579:
1574:
1569:
1563:
1561:
1556:Carbon-carbon
1553:
1552:
1547:
1541:
1540:
1535:
1533:Zaitsev's rule
1530:
1525:
1520:
1515:
1510:
1505:
1500:
1495:
1490:
1485:
1480:
1478:Steric effects
1475:
1470:
1465:
1460:
1455:
1450:
1445:
1440:
1435:
1430:
1425:
1420:
1415:
1410:
1405:
1400:
1395:
1390:
1385:
1380:
1375:
1370:
1365:
1360:
1355:
1350:
1345:
1340:
1335:
1330:
1325:
1320:
1315:
1310:
1305:
1300:
1295:
1290:
1285:
1280:
1275:
1270:
1265:
1260:
1255:
1250:
1245:
1240:
1235:
1230:
1225:
1220:
1215:
1210:
1205:
1200:
1195:
1190:
1185:
1180:
1175:
1170:
1165:
1159:
1156:
1155:
1153:
1152:
1147:
1142:
1137:
1132:
1130:Redox reaction
1127:
1122:
1117:
1115:Polymerization
1112:
1107:
1101:
1098:
1097:
1091:
1089:
1088:
1081:
1074:
1066:
1060:
1059:
1048:
1037:
1024:
1023:External links
1021:
1018:
1017:
989:
961:
938:
927:(4): 415–430.
903:
882:(2): 307–353.
861:
821:
802:
768:
767:
765:
762:
761:
760:
758:Hirao coupling
755:
750:
745:
738:
735:
692:
644:
616:
613:
574:
570:
547:
546:
531:
525:
507:
506:
490:
482:
475:
468:
461:
450:
442:
412:
409:
407:
404:
362:
352:
348:
336:
332:
328:
324:
316:
308:
304:
300:
294:
284:
280:
268:
264:
247:alkyl halide (
230:
216:
213:
204:
200:
196:
192:
188:
184:
81:
80:
77:
76:
69:
62:
61:
54:
50:
49:
45:
44:
39:
38:Reaction type
35:
34:
25:
21:
20:
13:
10:
9:
6:
4:
3:
2:
4403:
4392:
4389:
4387:
4384:
4382:
4379:
4378:
4376:
4353:
4350:
4348:
4345:
4343:
4340:
4338:
4335:
4333:
4330:
4328:
4325:
4323:
4320:
4318:
4315:
4313:
4310:
4308:
4305:
4303:
4300:
4298:
4295:
4293:
4290:
4288:
4285:
4283:
4280:
4278:
4275:
4273:
4272:Herz reaction
4270:
4268:
4265:
4263:
4260:
4258:
4255:
4253:
4250:
4248:
4245:
4243:
4240:
4238:
4235:
4233:
4230:
4228:
4225:
4223:
4220:
4218:
4215:
4213:
4210:
4208:
4205:
4203:
4200:
4198:
4195:
4193:
4190:
4188:
4185:
4183:
4180:
4178:
4175:
4173:
4170:
4168:
4165:
4163:
4160:
4158:
4155:
4153:
4150:
4149:
4147:
4143:
4137:
4134:
4132:
4129:
4127:
4124:
4122:
4119:
4117:
4114:
4112:
4109:
4107:
4104:
4102:
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:
3978:
3976:
3974:
3973:Cycloaddition
3970:
3964:
3961:
3959:
3956:
3954:
3951:
3949:
3946:
3944:
3941:
3939:
3936:
3934:
3931:
3929:
3926:
3924:
3921:
3919:
3916:
3914:
3911:
3909:
3906:
3904:
3901:
3899:
3896:
3894:
3891:
3889:
3886:
3884:
3881:
3879:
3876:
3874:
3871:
3869:
3866:
3864:
3861:
3859:
3856:
3854:
3851:
3849:
3846:
3844:
3841:
3839:
3836:
3834:
3831:
3829:
3826:
3824:
3821:
3819:
3818:Isay reaction
3816:
3814:
3811:
3809:
3806:
3804:
3801:
3799:
3796:
3794:
3791:
3789:
3786:
3784:
3781:
3779:
3776:
3774:
3771:
3769:
3766:
3764:
3761:
3759:
3756:
3754:
3751:
3749:
3746:
3744:
3741:
3739:
3736:
3734:
3731:
3729:
3726:
3724:
3721:
3719:
3716:
3714:
3713:Cycloaddition
3711:
3709:
3706:
3704:
3701:
3699:
3696:
3694:
3691:
3689:
3686:
3684:
3681:
3679:
3676:
3674:
3671:
3669:
3666:
3664:
3661:
3659:
3656:
3654:
3651:
3649:
3646:
3644:
3641:
3639:
3636:
3634:
3631:
3629:
3626:
3624:
3621:
3619:
3616:
3615:
3613:
3611:
3608:Ring forming
3605:
3599:
3596:
3594:
3591:
3589:
3586:
3584:
3581:
3579:
3576:
3574:
3571:
3569:
3566:
3564:
3561:
3559:
3556:
3554:
3551:
3549:
3546:
3544:
3541:
3539:
3536:
3534:
3531:
3529:
3526:
3524:
3521:
3519:
3516:
3514:
3511:
3509:
3508:Rupe reaction
3506:
3504:
3501:
3499:
3496:
3494:
3491:
3489:
3486:
3484:
3481:
3479:
3476:
3474:
3471:
3469:
3466:
3464:
3461:
3459:
3456:
3454:
3451:
3449:
3446:
3444:
3441:
3439:
3436:
3434:
3431:
3429:
3426:
3424:
3421:
3419:
3416:
3414:
3411:
3409:
3406:
3404:
3401:
3399:
3396:
3394:
3391:
3389:
3386:
3384:
3381:
3379:
3376:
3374:
3371:
3369:
3366:
3364:
3361:
3359:
3356:
3354:
3351:
3349:
3346:
3344:
3341:
3339:
3336:
3334:
3331:
3329:
3326:
3324:
3321:
3319:
3316:
3314:
3311:
3309:
3306:
3304:
3301:
3299:
3296:
3294:
3291:
3289:
3286:
3284:
3281:
3279:
3276:
3274:
3271:
3269:
3266:
3264:
3261:
3259:
3256:
3254:
3251:
3249:
3246:
3244:
3241:
3239:
3236:
3234:
3231:
3229:
3226:
3224:
3221:
3219:
3216:
3214:
3211:
3209:
3206:
3204:
3201:
3199:
3196:
3194:
3191:
3189:
3186:
3184:
3181:
3179:
3176:
3174:
3171:
3169:
3166:
3164:
3161:
3159:
3156:
3154:
3151:
3149:
3146:
3144:
3141:
3139:
3136:
3134:
3131:
3130:
3128:
3126:
3120:
3114:
3111:
3109:
3106:
3104:
3101:
3099:
3096:
3094:
3091:
3089:
3086:
3084:
3081:
3079:
3076:
3074:
3071:
3069:
3066:
3064:
3061:
3059:
3056:
3054:
3051:
3049:
3046:
3044:
3041:
3039:
3036:
3034:
3031:
3029:
3026:
3024:
3021:
3019:
3016:
3014:
3011:
3009:
3006:
3004:
3001:
2999:
2996:
2994:
2991:
2989:
2986:
2984:
2981:
2979:
2976:
2974:
2971:
2969:
2966:
2964:
2961:
2959:
2956:
2954:
2951:
2949:
2946:
2944:
2941:
2939:
2936:
2934:
2931:
2929:
2926:
2924:
2921:
2919:
2916:
2914:
2911:
2909:
2906:
2904:
2901:
2899:
2898:Ley oxidation
2896:
2894:
2891:
2889:
2886:
2884:
2881:
2879:
2876:
2874:
2871:
2869:
2866:
2864:
2863:Hydroxylation
2861:
2859:
2856:
2854:
2853:Hydrogenation
2851:
2849:
2846:
2844:
2841:
2839:
2836:
2834:
2831:
2829:
2826:
2824:
2821:
2819:
2816:
2814:
2811:
2809:
2806:
2804:
2801:
2799:
2796:
2794:
2791:
2789:
2788:DNA oxidation
2786:
2784:
2781:
2779:
2778:Deoxygenation
2776:
2774:
2771:
2769:
2766:
2764:
2761:
2759:
2756:
2754:
2751:
2749:
2746:
2744:
2741:
2739:
2736:
2734:
2731:
2729:
2726:
2724:
2721:
2719:
2716:
2714:
2711:
2709:
2706:
2704:
2701:
2699:
2696:
2694:
2691:
2689:
2686:
2684:
2681:
2679:
2676:
2674:
2671:
2669:
2668:Aromatization
2666:
2664:
2661:
2659:
2656:
2654:
2651:
2649:
2646:
2644:
2641:
2639:
2636:
2634:
2631:
2629:
2626:
2625:
2623:
2621:
2615:
2609:
2606:
2604:
2601:
2599:
2596:
2594:
2591:
2589:
2586:
2584:
2581:
2579:
2576:
2574:
2571:
2569:
2566:
2564:
2561:
2559:
2556:
2554:
2551:
2549:
2546:
2544:
2541:
2540:
2538:
2532:
2526:
2523:
2521:
2518:
2516:
2513:
2511:
2508:
2506:
2505:Reed reaction
2503:
2501:
2498:
2496:
2493:
2491:
2488:
2486:
2483:
2481:
2478:
2476:
2473:
2471:
2468:
2466:
2463:
2461:
2458:
2456:
2453:
2451:
2448:
2446:
2443:
2441:
2438:
2436:
2433:
2431:
2428:
2426:
2423:
2422:
2420:
2416:bond forming
2412:
2402:
2399:
2397:
2394:
2392:
2389:
2387:
2384:
2382:
2379:
2377:
2374:
2372:
2369:
2367:
2364:
2362:
2359:
2357:
2354:
2352:
2349:
2347:
2344:
2342:
2339:
2337:
2334:
2332:
2329:
2327:
2324:
2322:
2321:Cope reaction
2319:
2317:
2314:
2312:
2309:
2307:
2304:
2302:
2299:
2298:
2296:
2292:
2286:
2283:
2281:
2278:
2276:
2273:
2271:
2268:
2266:
2263:
2261:
2258:
2256:
2253:
2252:
2250:
2248:
2244:
2238:
2235:
2233:
2230:
2228:
2225:
2223:
2220:
2218:
2215:
2213:
2210:
2208:
2205:
2203:
2200:
2198:
2195:
2193:
2190:
2188:
2185:
2183:
2180:
2178:
2175:
2173:
2170:
2168:
2165:
2163:
2160:
2158:
2155:
2153:
2150:
2148:
2145:
2143:
2140:
2138:
2135:
2133:
2130:
2128:
2125:
2123:
2120:
2118:
2115:
2113:
2110:
2108:
2105:
2103:
2100:
2098:
2095:
2093:
2090:
2088:
2085:
2083:
2080:
2078:
2075:
2073:
2070:
2068:
2065:
2063:
2060:
2058:
2055:
2053:
2050:
2048:
2045:
2043:
2040:
2038:
2035:
2033:
2032:Nef synthesis
2030:
2028:
2025:
2023:
2020:
2018:
2015:
2013:
2010:
2008:
2007:Methylenation
2005:
2003:
2000:
1998:
1995:
1993:
1990:
1988:
1985:
1983:
1980:
1978:
1975:
1973:
1970:
1968:
1965:
1963:
1960:
1958:
1955:
1953:
1950:
1948:
1945:
1943:
1940:
1938:
1935:
1933:
1930:
1928:
1925:
1923:
1920:
1918:
1915:
1913:
1910:
1908:
1905:
1903:
1900:
1898:
1895:
1893:
1890:
1888:
1885:
1883:
1880:
1878:
1877:Heck reaction
1875:
1873:
1870:
1868:
1865:
1863:
1860:
1858:
1855:
1853:
1850:
1848:
1845:
1843:
1840:
1838:
1835:
1833:
1830:
1828:
1825:
1823:
1820:
1818:
1815:
1813:
1810:
1808:
1805:
1803:
1800:
1798:
1795:
1793:
1790:
1788:
1785:
1783:
1780:
1778:
1775:
1773:
1770:
1768:
1765:
1763:
1760:
1758:
1755:
1753:
1750:
1748:
1745:
1743:
1740:
1738:
1735:
1733:
1730:
1728:
1725:
1723:
1720:
1718:
1715:
1713:
1710:
1708:
1705:
1703:
1700:
1698:
1695:
1693:
1690:
1688:
1685:
1683:
1680:
1678:
1675:
1673:
1670:
1668:
1665:
1663:
1660:
1658:
1655:
1653:
1650:
1648:
1645:
1643:
1640:
1638:
1635:
1633:
1630:
1628:
1625:
1623:
1620:
1618:
1615:
1613:
1610:
1608:
1605:
1603:
1600:
1598:
1595:
1593:
1590:
1588:
1585:
1583:
1580:
1578:
1575:
1573:
1570:
1568:
1565:
1564:
1562:
1558:bond forming
1554:
1550:
1545:
1539:
1536:
1534:
1531:
1529:
1526:
1524:
1523:Y-aromaticity
1521:
1519:
1516:
1514:
1511:
1509:
1508:Walsh diagram
1506:
1504:
1501:
1499:
1496:
1494:
1493:Taft equation
1491:
1489:
1486:
1484:
1481:
1479:
1476:
1474:
1471:
1469:
1466:
1464:
1463:Σ-aromaticity
1461:
1459:
1456:
1454:
1451:
1449:
1446:
1444:
1441:
1439:
1436:
1434:
1431:
1429:
1426:
1424:
1421:
1419:
1416:
1414:
1411:
1409:
1406:
1404:
1401:
1399:
1396:
1394:
1391:
1389:
1388:Marcus theory
1386:
1384:
1381:
1379:
1376:
1374:
1371:
1369:
1366:
1364:
1363:Hückel's rule
1361:
1359:
1356:
1354:
1351:
1349:
1346:
1344:
1341:
1339:
1336:
1334:
1331:
1329:
1326:
1324:
1321:
1319:
1318:Evelyn effect
1316:
1314:
1311:
1309:
1306:
1304:
1301:
1299:
1298:Electron-rich
1296:
1294:
1291:
1289:
1286:
1284:
1281:
1279:
1276:
1274:
1271:
1269:
1266:
1264:
1261:
1259:
1256:
1254:
1251:
1249:
1246:
1244:
1241:
1239:
1236:
1234:
1231:
1229:
1226:
1224:
1221:
1219:
1216:
1214:
1213:Bema Hapothle
1211:
1209:
1206:
1204:
1201:
1199:
1196:
1194:
1191:
1189:
1186:
1184:
1181:
1179:
1176:
1174:
1171:
1169:
1166:
1164:
1161:
1160:
1157:
1151:
1148:
1146:
1143:
1141:
1138:
1136:
1133:
1131:
1128:
1126:
1123:
1121:
1118:
1116:
1113:
1111:
1108:
1106:
1103:
1102:
1099:
1095:
1087:
1082:
1080:
1075:
1073:
1068:
1067:
1064:
1057:
1053:
1049:
1046:
1042:
1038:
1035:
1031:
1027:
1026:
1022:
1012:
1006:
1005:
1000:
993:
990:
985:
981:
977:
974:
973:
965:
962:
957:
953:
949:
948:J. Chem. Soc.
942:
939:
934:
930:
926:
923:
922:
914:
912:
910:
908:
904:
899:
895:
890:
885:
881:
878:
877:
872:
865:
862:
857:
844:
836:
832:
825:
822:
817:
813:
806:
803:
798:
794:
791:: 1048–1055.
790:
786:
785:
780:
773:
770:
763:
759:
756:
754:
751:
749:
746:
744:
741:
740:
736:
734:
730:
728:
724:
720:
716:
712:
707:
700:
696:
686:
682:
675:
671:
668:
663:
642:
623:
614:
609:
605:
602:
599:
594:
592:
591:isomerization
588:
584:
580:
568:
564:
560:
556:
552:
529:
523:
512:
511:
510:
488:
480:
473:
466:
459:
448:
440:
429:
428:
427:
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410:
405:
403:
401:
397:
393:
389:
385:
381:
376:
374:
370:
366:
358:
346:
342:
322:
314:
299:, where the R
298:
290:
278:
274:
262:
258:
254:
250:
246:
245:electrophilic
242:
238:
234:
221:
214:
212:
210:
195:} to give {(C
182:
178:
174:
170:
162:
158:
156:
152:
148:
144:
140:
136:
132:
128:
124:
120:
116:
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108:
104:
100:
96:
92:
88:
78:
74:
70:
67:
64:
63:
59:
55:
52:
51:
46:
43:
40:
37:
36:
33:
29:
26:
23:
22:
17:
3313:Ene reaction
2673:Autoxidation
2534:Degradation
2425:Azo coupling
2202:Ugi reaction
1802:Ene reaction
1602:Alkynylation
1453:Polyfluorene
1448:Polar effect
1313:Electrophile
1228:Bredt's rule
1198:Baird's rule
1168:Alpha effect
1051:
1040:
1029:
1010:
1002:
992:
978:(10): 2608.
975:
970:
964:
947:
941:
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919:
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874:
864:
852:|title=
843:cite journal
834:
830:
824:
815:
811:
805:
788:
782:
772:
731:
708:
704:
690:
679:
629:
603:
595:
579:acyl halides
559:heterocycles
548:
508:
425:
411:Alkyl halide
380:phosphoranes
377:
360:
276:
272:
256:
251:) to give a
248:
240:
237:nucleophilic
226:
209:Klaui ligand
177:phosphinates
166:
154:
146:
143:phosphinites
138:
135:phosphinates
130:
127:phosphonites
122:
119:phosphonates
114:
103:alkyl halide
90:
86:
84:
73:RXNO:0000060
68:ontology ID
48:Identifiers
24:Named after
1812:Ethenolysis
1458:Ring strain
1428:Nucleophile
1253:Clar's rule
1193:Aromaticity
831:Chem. Zentr
563:Iodobenzene
359:mechanism (
289:carbocation
107:pentavalent
4375:Categories
4096:Ozonolysis
3623:Annulation
2973:Ozonolysis
1092:Topics in
921:Chem. Rev.
764:References
587:chloroform
297:1 reaction
105:to form a
3610:reactions
3125:reactions
2620:reactions
2536:reactions
2418:reactions
1560:reactions
711:pyrolysis
643:−
573:2 or an S
474:≫
375:halides.
373:propargyl
313:neopentyl
99:trivalent
93:) is the
1503:Vinylogy
1173:Annulene
1120:Reagents
950:: 2550.
898:93719226
784:Berichte
737:See also
489:″
481:′
467:′
402:anions.
400:triflate
233:2 attack
1163:A value
1056:Article
1045:Article
1034:Article
837:: 1639.
715:Hydroxy
567:alkenes
351:1 and S
235:of the
896:
818:: 687.
619:": -->
555:trityl
415:": -->
261:halide
179:, and
141:) and
894:S2CID
727:amine
719:thiol
406:Scope
388:P NMR
369:allyl
341:vinyl
97:of a
856:help
621:edit
596:The
553:and
530:>
524:>
509:and
460:>
441:>
438:RCOX
417:edit
371:and
345:aryl
343:and
125:),
85:The
980:doi
952:doi
929:doi
884:doi
793:doi
639:ABP
533:RCl
527:RBr
471:CHX
445:RCH
398:or
203:)Co
191:)Co
157:).
66:RSC
4377::
1008:;
1001:.
976:79
925:81
906:^
892:.
873:.
847::
845:}}
841:{{
835:II
833:.
816:38
814:.
789:31
787:.
781:.
721:,
717:,
647:OR
521:RI
493:CX
478:RR
464:RR
365:2'
211:.
1085:e
1078:t
1071:v
1058:)
1047:)
1036:)
1015:.
986:.
982::
958:.
954::
935:.
931::
900:.
886::
880:9
858:)
854:(
799:.
795::
693:N
625:]
575:N
571:N
486:R
457:X
449:2
421:]
363:N
361:S
353:N
349:N
337:N
333:N
329:N
325:N
317:N
309:N
305:N
301:1
295:N
293:S
285:N
281:1
277:5
273:4
269:1
265:N
257:3
249:2
241:1
231:N
229:S
205:3
201:5
199:H
197:5
193:3
189:5
187:H
185:5
155:6
153:(
147:5
145:(
139:4
137:(
131:3
129:(
123:2
121:(
115:1
113:(
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