278:
231:
183:
210:
167:
98:, in which a pre-existing chiral center undergoes reaction with a chiral catalyst, an enzyme or a chiral reagent such that one enantiomer reacts faster than the other and leaves behind the less reactive enantiomer, or in which a pre-existing chiral center influences the reactivity of a reaction center elsewhere in the same molecule.
176:
predicts the major diastereomer resulting from the diastereoselective nucleophilic addition to a carbonyl group next to a chiral center. The chiral center need not be optically pure, as the relative stereochemistry will be the same for both enantiomers. In the example below the (S)-aldehyde reacts
109:
is formed in preference to another (or in which a subset of all possible diastereomers dominates the product mixture), establishing a preferred relative stereochemistry. In this case, either two or more chiral centers are formed at once such that one relative stereochemistry is favored, or a
137:), or asymmetric transformation (conversion of a racemate into a pure enantiomer or into a mixture in which one enantiomer is present in excess, or of a diastereoisomeric mixture into a single diastereoisomer or into a mixture in which one diastereoisomer predominates).
323:(a)"Overlap Control of Carbanionoid Reactions. I. Stereoselectivity in Alkaline Epoxidation," Zimmerman, H. E.; Singer, L.; Thyagarajan, B. S. J. Am. Chem. Soc., 1959, 81, 108-116. (b)Eliel, E., "Stereochemistry of Carbon Compound", McGraw-Hill, 1962 pp 434-436.
220:
center next to the carbocation the substitution can be stereoselective in inter- and intramolecular reactions. In the reaction depicted below the nucleophile (furan) can approach the carbocation formed from the least shielded side away from the bulky
74:
difference between the two pathways is finite: both products are at least possible and merely differ in amount. However, in favorable cases, the minor stereoisomer may not be detectable by the analytic methods used.
277:
123:
The quality of stereoselectivity is concerned solely with the products, and their stereochemistry. Of a number of possible stereoisomeric products, the reaction selects one or two to be formed.
3746:
110:
pre-existing chiral center (which needs not be optically pure) biases the stereochemical outcome during the creation of another. The degree of relative selectivity is measured by the
2862:
230:
2807:
3575:
491:
Davin LB, Wang HB, Crowell AL, et al. (1997). "Stereoselective bimolecular phenoxy radical coupling by an auxiliary (dirigent) protein without an active center".
2917:
134:
182:
86:
is formed in preference to the other, in a reaction that creates an optically active product from an achiral starting material, using either a chiral catalyst, an
3067:
1701:
3796:
3570:
2672:
1396:
2442:
593:
3242:
1186:
3337:
1441:
3317:
2812:
1979:
1860:
1416:
200:
substrate is transformed into an optically active epoxyalcohol. In the case of chiral allylic alcohols, kinetic resolution results. Another example is
3407:
3162:
629:
209:
1994:
3640:
3097:
3590:
3202:
3182:
3142:
1949:
3736:
3661:
3545:
2157:
1561:
892:
3731:
3560:
3217:
3072:
2702:
2547:
1784:
201:
2907:
2397:
2072:
120:
can be considered an opposite of stereospecificity, when the reaction of two different stereoisomers yield a single product stereoisomer.
3811:
3595:
2617:
3172:
166:
3806:
3520:
3382:
3137:
3696:
3167:
3082:
3052:
3032:
2897:
2892:
2267:
2192:
1835:
1789:
1656:
917:
3635:
3801:
3761:
3711:
3187:
2937:
2867:
1356:
3397:
3002:
1895:
1616:
3387:
927:
3555:
3312:
3262:
2052:
1984:
1875:
1451:
1206:
1131:
912:
3267:
3077:
2552:
2462:
586:
3841:
3625:
3565:
2967:
2942:
2852:
2432:
2312:
1346:
842:
3726:
3212:
3007:
1276:
3831:
3417:
2927:
2437:
2382:
2227:
2187:
2019:
1774:
1491:
1341:
3791:
3352:
3307:
2797:
2652:
3826:
3741:
3600:
3515:
3412:
2487:
2142:
1810:
1221:
782:
3716:
3691:
3676:
3372:
3237:
3192:
2957:
2502:
2352:
1566:
1246:
1191:
3721:
3666:
3197:
2612:
2327:
2322:
1815:
1631:
1621:
1336:
1196:
1146:
1141:
1116:
1022:
3776:
3377:
3297:
2912:
2877:
2722:
2147:
2107:
2004:
1779:
1531:
1476:
1076:
787:
777:
752:
3751:
3452:
3257:
2692:
2257:
2232:
2172:
1764:
1471:
1121:
1306:
3042:
2577:
2029:
1251:
1216:
812:
747:
579:
536:"An Enantiocomplementary Dirigent Protein for the Enantioselective Laccase-Catalyzed Oxidative Coupling of Phenols"
3610:
3232:
2292:
2217:
1741:
1576:
1261:
1037:
997:
742:
3851:
3756:
3490:
3462:
3432:
3347:
3277:
3207:
3127:
3027:
2987:
2682:
2302:
1601:
1596:
1058:
922:
3816:
3686:
3550:
3392:
3252:
2772:
1746:
1296:
1256:
1007:
415:
Diastereoselective
Friedel-Crafts Cyclization Reactions to 2-Substituted 1-Phenyl-1,2,3,4-tetrahydronaphthalenes
58:
or during a non-stereospecific transformation of a pre-existing one. The selectivity arises from differences in
3890:
3706:
3302:
3272:
3147:
3102:
2932:
2842:
2657:
2647:
2477:
2034:
1974:
1939:
1726:
1686:
1461:
1331:
847:
837:
767:
3282:
2262:
1286:
832:
712:
3495:
3786:
3645:
3437:
3362:
3342:
3062:
3012:
2872:
2837:
2777:
2707:
2009:
1989:
1721:
1641:
1536:
1496:
1466:
1401:
1271:
1181:
1171:
1047:
757:
289:
70:
leading to the different products. Stereoselectivity can vary in degree but it can never be total since the
354:
Eliel, E.L. & Willen S.H., "Stereochemistry of
Organic Compounds", John Wiley & Sons, 2008 pp 1209.
3525:
3247:
2997:
2977:
2952:
2902:
2817:
2792:
2747:
2717:
2697:
2667:
2632:
2587:
2562:
2537:
2422:
2347:
2127:
1820:
1756:
1556:
1281:
1201:
887:
862:
639:
634:
3861:
2607:
1231:
129:
is a general term for the conversion of one stereoisomer into another. For example, racemization (as in S
3447:
3402:
3117:
3087:
3057:
2992:
2972:
2887:
2882:
2847:
2802:
2787:
2782:
2762:
2752:
2687:
2677:
2557:
2077:
1880:
1456:
1411:
1241:
977:
697:
659:
468:
194:
190:
111:
907:
902:
3500:
3630:
3580:
3530:
3510:
3357:
3332:
3047:
3037:
2922:
2737:
2732:
2662:
2447:
2247:
2207:
2137:
2102:
2057:
2024:
1890:
1865:
1845:
1666:
1626:
1586:
1551:
1481:
1236:
1106:
1081:
619:
269:
251:
3846:
3836:
3821:
3467:
3442:
3427:
3422:
3152:
3107:
3092:
2982:
2962:
2857:
2742:
2727:
2572:
2517:
2507:
2497:
2472:
2237:
2112:
2087:
1999:
1855:
1840:
1825:
1681:
1646:
1591:
1361:
1211:
1156:
1027:
942:
802:
727:
177:
with a thiazole to form the (S,S) diastereomer but only a small amount of the (S,R) diastereomer:
146:
91:
872:
438:
3585:
3535:
3505:
3367:
3157:
2947:
2832:
2767:
2757:
2522:
2452:
2417:
2412:
2392:
2387:
2332:
2242:
2092:
1954:
1944:
1850:
1636:
1581:
1511:
1431:
1326:
1226:
1161:
1086:
932:
797:
732:
557:
516:
95:
67:
63:
717:
3322:
2642:
2527:
2492:
2457:
2402:
2357:
2317:
2272:
2252:
2202:
2197:
2167:
2152:
2062:
1969:
1905:
1870:
1696:
1571:
1446:
1371:
1351:
1266:
1101:
1096:
1042:
952:
857:
817:
772:
654:
614:
508:
441:
367:
294:
260:
71:
51:
39:
161:
are also classified as diastereomers, this reaction would also be called diastereoselective.
3856:
3701:
3671:
3615:
3540:
3472:
3227:
3177:
3022:
2827:
2602:
2597:
2542:
2532:
2307:
2117:
2097:
2067:
1964:
1900:
1885:
1716:
1671:
1661:
1651:
1546:
1526:
1521:
1506:
1501:
1381:
1376:
1316:
1301:
1291:
1136:
1126:
992:
982:
972:
882:
877:
852:
792:
644:
603:
547:
500:
475:
449:
422:
375:
304:
299:
264:
246:
158:
204:. In the example below the achiral alkene yields only one of the possible 4 stereoisomers.
3766:
3457:
3292:
3287:
2582:
2567:
2512:
2467:
2427:
2377:
2342:
2337:
2282:
2277:
2212:
2162:
2082:
1910:
1794:
1769:
1731:
1706:
1691:
1676:
1611:
1486:
1436:
1426:
1406:
1366:
1176:
1166:
1151:
947:
867:
692:
687:
197:
47:
737:
707:
3771:
3681:
3620:
2712:
2622:
2592:
2367:
2222:
1959:
1736:
1606:
1421:
1391:
1091:
987:
762:
624:
173:
59:
534:
Pickel B, Constantin M-A, Pfannsteil J, Conrad J, Beifuss U, Schaffer A (March 2007).
3884:
3781:
3482:
3327:
3222:
3017:
2407:
2372:
2362:
2297:
2287:
2177:
2014:
1830:
1541:
1516:
1386:
1032:
1017:
1002:
897:
827:
807:
722:
561:
520:
2822:
2182:
1934:
1711:
1311:
1111:
962:
957:
822:
677:
106:
55:
504:
133:
1 reactions), epimerization (as in interconversion of D-glucose and D-mannose in
1321:
967:
937:
702:
256:
255:. This protein has been found to direct the stereoselective biosynthesis of (+)-
242:
217:
403:
391:
17:
3605:
3132:
2482:
571:
552:
535:
364:
Effects of base strength and size upon in base-promoted elimination reactions.
83:
27:
Ability of a chemical reaction to produce an unequal mixture of stereoisomers
336:
1 reaction destroys a pre-existing stereocenter, and then creates a new one.
31:
479:
512:
426:
1012:
682:
43:
379:
672:
366:
Richard A. Bartsch, Gerald M. Pruss, Bruce A. Bushaw, Karl E. Wiegers
222:
453:
390:
Organic
Syntheses, Coll. Vol. 10, p.140 (2004); Vol. 77, p.78 (2000).
402:
Organic
Syntheses, Coll. Vol. 10, p.603 (2004); Vol. 79, p.93 (2002).
87:
345:
Or fewer than all possible relative stereochemistries are obtained.
90:
or a chiral reagent. The degree of selectivity is measured by the
1056:
575:
273:, which directs enantioselective synthesis of (−)-pinoresinol.
193:
is an example of an enantioselective process, in which an
440:
Friedrich Mühlthau, Oliver
Schuster, and Thorsten Bach
465:
Stereoselective
Reactions with Stabilized Carbocations
225:
group resulting in high facial diastereoselectivity:
3747:
Erlenmeyer–Plöchl azlactone and amino-acid synthesis
3654:
3481:
3116:
2631:
2126:
2043:
1923:
1803:
1755:
1065:
263:monomers. Recently, a second, enantiocomplementary
2808:Divinylcyclopropane-cycloheptadiene rearrangement
249:. The first dirigent protein was discovered in
3068:Thermal rearrangement of aromatic hydrocarbons
1702:Thermal rearrangement of aromatic hydrocarbons
145:An example of modest stereoselectivity is the
3797:Lectka enantioselective beta-lactam synthesis
587:
8:
3576:Inverse electron-demand Diels–Alder reaction
1397:Heterogeneous metal catalyzed cross-coupling
417:Friedrich Mühlthau, Thorsten Bach Synthesis
2918:Lobry de Bruyn–Van Ekenstein transformation
135:Lobry de Bruyn–Van Ekenstein transformation
3478:
1752:
1053:
594:
580:
572:
3408:Petrenko-Kritschenko piperidone synthesis
2863:Fritsch–Buttenberg–Wiechell rearrangement
551:
245:biosynthesis involved a protein called a
3571:Intramolecular Diels–Alder cycloaddition
316:
3591:Metal-centered cycloaddition reactions
3243:Debus–Radziszewski imidazole synthesis
1187:Bodroux–Chichibabin aldehyde synthesis
467:Pier Giorgio Cozzi and Fides Benfatti
3737:Diazoalkane 1,3-dipolar cycloaddition
3641:Vinylcyclopropane (5+2) cycloaddition
3546:Diazoalkane 1,3-dipolar cycloaddition
3318:Hurd–Mori 1,2,3-thiadiazole synthesis
2813:Dowd–Beckwith ring-expansion reaction
1980:Hurd–Mori 1,2,3-thiadiazole synthesis
893:LFER solvent coefficients (data page)
7:
2548:Sharpless asymmetric dihydroxylation
1785:Methoxymethylenetriphenylphosphorane
202:Sharpless asymmetric dihydroxylation
2673:Allen–Millar–Trippett rearrangement
3812:Nitrone-olefin (3+2) cycloaddition
3807:Niementowski quinazoline synthesis
3596:Nitrone-olefin (3+2) cycloaddition
3521:Azide-alkyne Huisgen cycloaddition
3383:Niementowski quinazoline synthesis
3138:Azide-alkyne Huisgen cycloaddition
2443:Meerwein–Ponndorf–Verley reduction
1995:Leimgruber–Batcho indole synthesis
25:
3636:Trimethylenemethane cycloaddition
3338:Johnson–Corey–Chaykovsky reaction
3203:Cadogan–Sundberg indole synthesis
3183:Bohlmann–Rahtz pyridine synthesis
3143:Baeyer–Emmerling indole synthesis
1950:Cadogan–Sundberg indole synthesis
1442:Johnson–Corey–Chaykovsky reaction
149:of 2-iodobutane which yields 60%
3732:Cook–Heilbron thiazole synthesis
3561:Hexadehydro Diels–Alder reaction
3388:Niementowski quinoline synthesis
3218:Cook–Heilbron thiazole synthesis
3163:Bischler–Möhlau indole synthesis
3073:Tiffeneau–Demjanov rearrangement
2703:Baker–Venkataraman rearrangement
1861:Horner–Wadsworth–Emmons reaction
1532:Mizoroki-Heck vs. Reductive Heck
1417:Horner–Wadsworth–Emmons reaction
928:Neighbouring group participation
276:
229:
208:
181:
165:
3268:Fiesselmann thiophene synthesis
3098:Westphalen–Lettré rearrangement
3078:Vinylcyclopropane rearrangement
2908:Kornblum–DeLaMare rearrangement
2553:Epoxidation of allylic alcohols
2463:Noyori asymmetric hydrogenation
2398:Kornblum–DeLaMare rearrangement
2073:Gallagher–Hollander degradation
3727:Chichibabin pyridine synthesis
3213:Chichibabin pyridine synthesis
3173:Blum–Ittah aziridine synthesis
3008:Ring expansion and contraction
1277:Cross dehydrogenative coupling
1:
3697:Bischler–Napieralski reaction
3655:Heterocycle forming reactions
3308:Hemetsberger indole synthesis
3168:Bischler–Napieralski reaction
3083:Wagner–Meerwein rearrangement
3053:Sommelet–Hauser rearrangement
3033:Seyferth–Gilbert homologation
2898:Ireland–Claisen rearrangement
2893:Hofmann–Martius rearrangement
2653:2,3-sigmatropic rearrangement
2268:Corey–Winter olefin synthesis
2193:Barton–McCombie deoxygenation
1836:Corey–Winter olefin synthesis
1790:Seyferth–Gilbert homologation
1657:Seyferth–Gilbert homologation
105:reaction is one in which one
82:reaction is one in which one
3802:Lehmstedt–Tanasescu reaction
3762:Gabriel–Colman rearrangement
3717:Bucherer carbazole synthesis
3712:Borsche–Drechsel cyclization
3692:Bernthsen acridine synthesis
3677:Bamberger triazine synthesis
3662:Algar–Flynn–Oyamada reaction
3373:Nazarov cyclization reaction
3238:De Kimpe aziridine synthesis
3193:Bucherer carbazole synthesis
3188:Borsche–Drechsel cyclization
2958:Nazarov cyclization reaction
2938:Meyer–Schuster rearrangement
2868:Gabriel–Colman rearrangement
2618:Wolffenstein–Böters reaction
2503:Reduction of nitro compounds
2353:Grundmann aldehyde synthesis
2158:Algar–Flynn–Oyamada reaction
1567:Olefin conversion technology
1562:Nozaki–Hiyama–Kishi reaction
1357:Gabriel–Colman rearrangement
1247:Claisen-Schmidt condensation
1192:Bouveault aldehyde synthesis
505:10.1126/science.275.5298.362
238:Stereoselective biosynthesis
46:forms an unequal mixture of
3777:Hantzsch pyridine synthesis
3556:Enone–alkene cycloadditions
3378:Nenitzescu indole synthesis
3298:Hantzsch pyridine synthesis
3263:Ferrario–Ackermann reaction
2913:Kowalski ester homologation
2878:Halogen dance rearrangement
2723:Benzilic acid rearrangement
2148:Akabori amino-acid reaction
2108:Von Braun amide degradation
2053:Barbier–Wieland degradation
2005:Nenitzescu indole synthesis
1985:Kharasch–Sosnovsky reaction
1876:Julia–Kocienski olefination
1780:Kowalski ester homologation
1477:Kowalski ester homologation
1452:Julia–Kocienski olefination
1207:Cadiot–Chodkiewicz coupling
1132:Aza-Baylis–Hillman reaction
1077:Acetoacetic ester synthesis
788:Dynamic binding (chemistry)
778:Conrotatory and disrotatory
753:Charge remote fragmentation
3907:
3842:Robinson–Gabriel synthesis
3792:Kröhnke pyridine synthesis
3626:Retro-Diels–Alder reaction
3566:Imine Diels–Alder reaction
3353:Kröhnke pyridine synthesis
2968:Newman–Kwart rearrangement
2943:Mislow–Evans rearrangement
2853:Fischer–Hepp rearrangement
2798:Di-π-methane rearrangement
2578:Stephen aldehyde synthesis
2313:Eschweiler–Clarke reaction
2030:Williamson ether synthesis
1347:Fujiwara–Moritani reaction
1252:Combes quinoline synthesis
1217:Carbonyl olefin metathesis
918:More O'Ferrall–Jencks plot
843:Grunwald–Winstein equation
813:Electron-withdrawing group
748:Catalytic resonance theory
94:. An important variant is
3852:Urech hydantoin synthesis
3832:Pomeranz–Fritsch reaction
3757:Fischer oxazole synthesis
3491:1,3-Dipolar cycloaddition
3463:Urech hydantoin synthesis
3433:Reissert indole synthesis
3418:Pomeranz–Fritsch reaction
3348:Knorr quinoline synthesis
3278:Fischer oxazole synthesis
3208:Camps quinoline synthesis
3128:1,3-Dipolar cycloaddition
3028:Semipinacol rearrangement
3003:Ramberg–Bäcklund reaction
2988:Piancatelli rearrangement
2928:McFadyen–Stevens reaction
2683:Alpha-ketol rearrangement
2438:McFadyen–Stevens reaction
2383:Kiliani–Fischer synthesis
2303:Elbs persulfate oxidation
2228:Bouveault–Blanc reduction
2188:Baeyer–Villiger oxidation
2020:Schotten–Baumann reaction
1896:Ramberg–Bäcklund reaction
1775:Kiliani–Fischer synthesis
1617:Ramberg–Bäcklund reaction
1602:Pinacol coupling reaction
1597:Piancatelli rearrangement
1492:Liebeskind–Srogl coupling
1342:Fujimoto–Belleau reaction
1059:List of organic reactions
923:Negative hyperconjugation
668:
610:
553:10.1007/s10086-007-0892-x
448:, 127 (26), pp 9348–9349
3827:Pictet–Spengler reaction
3742:Einhorn–Brunner reaction
3707:Boger pyridine synthesis
3601:Oxo-Diels–Alder reaction
3516:Aza-Diels–Alder reaction
3413:Pictet–Spengler reaction
3313:Hofmann–Löffler reaction
3303:Hegedus indole synthesis
3273:Fischer indole synthesis
3148:Bartoli indole synthesis
3103:Willgerodt rearrangement
2933:McLafferty rearrangement
2843:Ferrier carbocyclization
2658:2,3-Wittig rearrangement
2648:1,2-Wittig rearrangement
2488:Parikh–Doering oxidation
2478:Oxygen rebound mechanism
2143:Adkins–Peterson reaction
2035:Yamaguchi esterification
1975:Hegedus indole synthesis
1940:Bartoli indole synthesis
1811:Bamford–Stevens reaction
1727:Weinreb ketone synthesis
1687:Stork enamine alkylation
1462:Knoevenagel condensation
1332:Ferrier carbocyclization
1222:Castro–Stephens coupling
848:Hammett acidity function
838:Free-energy relationship
783:Curtin–Hammett principle
768:Conformational isomerism
157:-2-butene. Since alkene
3787:Knorr pyrrole synthesis
3722:Bucherer–Bergs reaction
3667:Allan–Robinson reaction
3646:Wagner-Jauregg reaction
3438:Ring-closing metathesis
3363:Larock indole synthesis
3343:Knorr pyrrole synthesis
3198:Bucherer–Bergs reaction
3063:Stieglitz rearrangement
3043:Skattebøl rearrangement
3013:Ring-closing metathesis
2873:Group transfer reaction
2838:Favorskii rearrangement
2778:Cornforth rearrangement
2708:Bamberger rearrangement
2613:Wolff–Kishner reduction
2433:Markó–Lam deoxygenation
2328:Fleming–Tamao oxidation
2323:Fischer–Tropsch process
2010:Oxymercuration reaction
1990:Knorr pyrrole synthesis
1816:Barton–Kellogg reaction
1722:Wagner-Jauregg reaction
1642:Ring-closing metathesis
1632:Reimer–Tiemann reaction
1622:Rauhut–Currier reaction
1537:Nef isocyanide reaction
1497:Malonic ester synthesis
1467:Knorr pyrrole synthesis
1402:High dilution principle
1337:Friedel–Crafts reaction
1272:Cross-coupling reaction
1197:Bucherer–Bergs reaction
1182:Blanc chloromethylation
1172:Blaise ketone synthesis
1147:Baylis–Hillman reaction
1142:Barton–Kellogg reaction
1117:Allan–Robinson reaction
1023:Woodward–Hoffmann rules
758:Charge-transfer complex
290:Dynamic stereochemistry
3752:Feist–Benary synthesis
3526:Bradsher cycloaddition
3496:4+4 Photocycloaddition
3453:Simmons–Smith reaction
3398:Paternò–Büchi reaction
3258:Feist–Benary synthesis
3248:Dieckmann condensation
2998:Pummerer rearrangement
2978:Oxy-Cope rearrangement
2953:Myers allene synthesis
2903:Jacobsen rearrangement
2818:Electrocyclic reaction
2793:Demjanov rearrangement
2748:Buchner ring expansion
2718:Beckmann rearrangement
2698:Aza-Cope rearrangement
2693:Arndt–Eistert reaction
2668:Alkyne zipper reaction
2588:Transfer hydrogenation
2563:Sharpless oxyamination
2538:Selenoxide elimination
2423:Lombardo methylenation
2348:Griesbaum coozonolysis
2258:Corey–Itsuno reduction
2233:Boyland–Sims oxidation
2173:Angeli–Rimini reaction
1821:Boord olefin synthesis
1765:Arndt–Eistert reaction
1757:Homologation reactions
1557:Nitro-Mannich reaction
1472:Kolbe–Schmitt reaction
1282:Cross-coupling partner
1202:Buchner ring expansion
1122:Arndt–Eistert reaction
888:Kinetic isotope effect
635:Rearrangement reaction
480:10.1002/anie.200905235
3611:Pauson–Khand reaction
3448:Sharpless epoxidation
3403:Pechmann condensation
3283:Friedländer synthesis
3233:Davis–Beirut reaction
3088:Wallach rearrangement
3058:Stevens rearrangement
2993:Pinacol rearrangement
2973:Overman rearrangement
2888:Hofmann rearrangement
2883:Hayashi rearrangement
2848:Ferrier rearrangement
2803:Dimroth rearrangement
2788:Curtius rearrangement
2783:Criegee rearrangement
2763:Claisen rearrangement
2753:Carroll rearrangement
2688:Amadori rearrangement
2678:Allylic rearrangement
2558:Sharpless epoxidation
2293:Dess–Martin oxidation
2218:Bohn–Schmidt reaction
2078:Hofmann rearrangement
1881:Kauffmann olefination
1804:Olefination reactions
1742:Wurtz–Fittig reaction
1577:Palladium–NHC complex
1457:Kauffmann olefination
1412:Homologation reaction
1262:Corey–House synthesis
1242:Claisen rearrangement
1038:Yukawa–Tsuno equation
998:Swain–Lupton equation
978:Spherical aromaticity
913:Möbius–Hückel concept
698:Aromatic ring current
660:Substitution reaction
469:Angew. Chem. Int. Ed.
427:10.1055/s-2005-918482
374:; 95(10); 3405-3407.
191:Sharpless epoxidation
112:diastereomeric excess
38:is the property of a
3817:Paal–Knorr synthesis
3687:Barton–Zard reaction
3631:Staudinger synthesis
3581:Ketene cycloaddition
3551:Diels–Alder reaction
3531:Cheletropic reaction
3511:Alkyne trimerisation
3393:Paal–Knorr synthesis
3358:Kulinkovich reaction
3333:Jacobsen epoxidation
3253:Diels–Alder reaction
3048:Smiles rearrangement
3038:Sigmatropic reaction
2923:Lossen rearrangement
2773:Corey–Fuchs reaction
2738:Boekelheide reaction
2733:Bergmann degradation
2663:Achmatowicz reaction
2448:Methionine sulfoxide
2248:Clemmensen reduction
2208:Bergmann degradation
2138:Acyloin condensation
2103:Strecker degradation
2058:Bergmann degradation
2025:Ullmann condensation
1891:Peterson olefination
1866:Hydrazone iodination
1846:Elimination reaction
1747:Zincke–Suhl reaction
1667:Sonogashira coupling
1627:Reformatsky reaction
1587:Peterson olefination
1552:Nierenstein reaction
1482:Kulinkovich reaction
1297:Diels–Alder reaction
1257:Corey–Fuchs reaction
1237:Claisen condensation
1107:Alkyne trimerisation
1082:Acyloin condensation
1048:Σ-bishomoaromaticity
1008:Thorpe–Ingold effect
620:Elimination reaction
311:Notes and references
270:Arabidopsis thaliana
252:Forsythia intermedia
68:mechanistic pathways
3837:Prilezhaev reaction
3822:Pellizzari reaction
3501:(4+3) cycloaddition
3468:Van Leusen reaction
3443:Robinson annulation
3428:Pschorr cyclization
3423:Prilezhaev reaction
3153:Bergman cyclization
3108:Wolff rearrangement
3093:Weerman degradation
2983:Pericyclic reaction
2963:Neber rearrangement
2858:Fries rearrangement
2743:Brook rearrangement
2728:Bergman cyclization
2573:Staudinger reaction
2518:Rosenmund reduction
2508:Reductive amination
2473:Oppenauer oxidation
2263:Corey–Kim oxidation
2238:Cannizzaro reaction
2113:Weerman degradation
2088:Isosaccharinic acid
2000:Mukaiyama hydration
1856:Hofmann elimination
1841:Dehydrohalogenation
1826:Chugaev elimination
1647:Robinson annulation
1592:Pfitzinger reaction
1362:Gattermann reaction
1307:Wulff–Dötz reaction
1287:Dakin–West reaction
1212:Carbonyl allylation
1157:Bergman cyclization
943:Kennedy J. P. Orton
863:Hammond's postulate
833:Flippin–Lodge angle
803:Electromeric effect
728:Beta-silicon effect
713:Baker–Nathan effect
380:10.1021/ja00791a067
332:For instance, the S
147:dehydrohalogenation
92:enantiomeric excess
3586:McCormack reaction
3536:Conia-ene reaction
3368:Madelung synthesis
3158:Biginelli reaction
2948:Mumm rearrangement
2833:Favorskii reaction
2768:Cope rearrangement
2758:Chan rearrangement
2523:Rubottom oxidation
2453:Miyaura borylation
2418:Lipid peroxidation
2413:Lindgren oxidation
2393:Kornblum oxidation
2388:Kolbe electrolysis
2333:Fukuyama reduction
2243:Carbonyl reduction
2093:Marker degradation
1955:Diazonium compound
1945:Boudouard reaction
1924:Carbon-heteroatom
1851:Grieco elimination
1637:Rieche formylation
1582:Passerini reaction
1512:Meerwein arylation
1432:Hydroxymethylation
1327:Favorskii reaction
1227:Chan rearrangement
1162:Biginelli reaction
1087:Aldol condensation
933:2-Norbornyl cation
908:Möbius aromaticity
903:Markovnikov's rule
798:Effective molarity
743:Bürgi–Dunitz angle
733:Bicycloaromaticity
267:was identified in
153:-2-butene and 20%
103:diastereoselective
96:kinetic resolution
64:electronic effects
54:creation of a new
42:in which a single
3878:
3877:
3874:
3873:
3870:
3869:
3862:Wohl–Aue reaction
3506:6+4 Cycloaddition
3323:Iodolactonization
2643:1,2-rearrangement
2608:Wohl–Aue reaction
2528:Sabatier reaction
2493:Pinnick oxidation
2458:Mozingo reduction
2403:Leuckart reaction
2358:Haloform reaction
2273:Criegee oxidation
2253:Collins oxidation
2203:Benkeser reaction
2198:Bechamp reduction
2168:Andrussow process
2153:Alcohol oxidation
2063:Edman degradation
1970:Haloform reaction
1919:
1918:
1906:Takai olefination
1871:Julia olefination
1697:Takai olefination
1572:Olefin metathesis
1447:Julia olefination
1372:Grignard reaction
1352:Fukuyama coupling
1267:Coupling reaction
1232:Chan–Lam coupling
1102:Alkyne metathesis
1097:Alkane metathesis
953:Phosphaethynolate
858:George S. Hammond
818:Electronic effect
773:Conjugated system
655:Stereospecificity
650:Stereoselectivity
615:Addition reaction
604:organic reactions
540:Angewandte Chemie
454:10.1021/ja050626v
442:J. Am. Chem. Soc.
368:J. Am. Chem. Soc.
295:Torquoselectivity
261:coniferyl alcohol
159:geometric isomers
118:Stereoconvergence
72:activation energy
40:chemical reaction
36:stereoselectivity
16:(Redirected from
3898:
3857:Wenker synthesis
3847:Stollé synthesis
3702:Bobbitt reaction
3672:Auwers synthesis
3616:Povarov reaction
3541:Cyclopropanation
3479:
3473:Wenker synthesis
3228:Darzens reaction
3178:Bobbitt reaction
3023:Schmidt reaction
2828:Enyne metathesis
2603:Whiting reaction
2598:Wharton reaction
2543:Shapiro reaction
2533:Sarett oxidation
2498:Prévost reaction
2308:Emde degradation
2118:Wohl degradation
2098:Ruff degradation
2068:Emde degradation
1965:Grignard reagent
1901:Shapiro reaction
1886:McMurry reaction
1753:
1717:Ullmann reaction
1682:Stollé synthesis
1672:Stetter reaction
1662:Shapiro reaction
1652:Sakurai reaction
1547:Negishi coupling
1527:Minisci reaction
1522:Michael reaction
1507:McMurry reaction
1502:Mannich reaction
1382:Hammick reaction
1377:Grignard reagent
1317:Enyne metathesis
1302:Doebner reaction
1292:Darzens reaction
1137:Barbier reaction
1127:Auwers synthesis
1054:
1028:Woodward's rules
993:Superaromaticity
983:Spiroaromaticity
883:Inductive effect
878:Hyperconjugation
853:Hammett equation
793:Edwards equation
645:Regioselectivity
596:
589:
582:
573:
566:
565:
555:
531:
525:
524:
488:
482:
462:
456:
435:
429:
412:
406:
400:
394:
388:
382:
361:
355:
352:
346:
343:
337:
330:
324:
321:
305:Chemoselectivity
300:Regioselectivity
280:
265:dirigent protein
247:dirigent protein
233:
212:
185:
169:
80:enantioselective
21:
3906:
3905:
3901:
3900:
3899:
3897:
3896:
3895:
3891:Stereochemistry
3881:
3880:
3879:
3866:
3767:Gewald reaction
3650:
3477:
3458:Skraup reaction
3293:Graham reaction
3288:Gewald reaction
3119:
3112:
2634:
2627:
2583:Swern oxidation
2568:Stahl oxidation
2513:Riley oxidation
2468:Omega oxidation
2428:Luche reduction
2378:Jones oxidation
2343:Glycol cleavage
2338:Ganem oxidation
2283:Davis oxidation
2278:Dakin oxidation
2213:Birch reduction
2163:Amide reduction
2129:
2122:
2083:Hooker reaction
2045:
2039:
1927:
1925:
1915:
1911:Wittig reaction
1799:
1795:Wittig reaction
1770:Hooker reaction
1751:
1732:Wittig reaction
1707:Thorpe reaction
1692:Suzuki reaction
1677:Stille reaction
1612:Quelet reaction
1487:Kumada coupling
1437:Ivanov reaction
1427:Hydrovinylation
1407:Hiyama coupling
1367:Glaser coupling
1177:Blaise reaction
1167:Bingel reaction
1152:Benary reaction
1069:
1067:
1061:
1052:
948:Passive binding
868:Homoaromaticity
718:Baldwin's rules
693:Antiaromaticity
688:Anomeric effect
664:
606:
600:
570:
569:
533:
532:
528:
499:(5298): 362–6.
490:
489:
485:
463:
459:
436:
432:
413:
409:
401:
397:
389:
385:
362:
358:
353:
349:
344:
340:
335:
331:
327:
322:
318:
313:
286:
240:
198:allylic alcohol
143:
132:
28:
23:
22:
18:Stereoselective
15:
12:
11:
5:
3904:
3902:
3894:
3893:
3883:
3882:
3876:
3875:
3872:
3871:
3868:
3867:
3865:
3864:
3859:
3854:
3849:
3844:
3839:
3834:
3829:
3824:
3819:
3814:
3809:
3804:
3799:
3794:
3789:
3784:
3779:
3774:
3772:Hantzsch ester
3769:
3764:
3759:
3754:
3749:
3744:
3739:
3734:
3729:
3724:
3719:
3714:
3709:
3704:
3699:
3694:
3689:
3684:
3682:Banert cascade
3679:
3674:
3669:
3664:
3658:
3656:
3652:
3651:
3649:
3648:
3643:
3638:
3633:
3628:
3623:
3621:Prato reaction
3618:
3613:
3608:
3603:
3598:
3593:
3588:
3583:
3578:
3573:
3568:
3563:
3558:
3553:
3548:
3543:
3538:
3533:
3528:
3523:
3518:
3513:
3508:
3503:
3498:
3493:
3487:
3485:
3476:
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:
3200:
3195:
3190:
3185:
3180:
3175:
3170:
3165:
3160:
3155:
3150:
3145:
3140:
3135:
3130:
3124:
3122:
3114:
3113:
3111:
3110:
3105:
3100:
3095:
3090:
3085:
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:
2855:
2850:
2845:
2840:
2835:
2830:
2825:
2820:
2815:
2810:
2805:
2800:
2795:
2790:
2785:
2780:
2775:
2770:
2765:
2760:
2755:
2750:
2745:
2740:
2735:
2730:
2725:
2720:
2715:
2713:Banert cascade
2710:
2705:
2700:
2695:
2690:
2685:
2680:
2675:
2670:
2665:
2660:
2655:
2650:
2645:
2639:
2637:
2633:Rearrangement
2629:
2628:
2626:
2625:
2623:Zinin reaction
2620:
2615:
2610:
2605:
2600:
2595:
2593:Wacker process
2590:
2585:
2580:
2575:
2570:
2565:
2560:
2555:
2550:
2545:
2540:
2535:
2530:
2525:
2520:
2515:
2510:
2505:
2500:
2495:
2490:
2485:
2480:
2475:
2470:
2465:
2460:
2455:
2450:
2445:
2440:
2435:
2430:
2425:
2420:
2415:
2410:
2405:
2400:
2395:
2390:
2385:
2380:
2375:
2370:
2368:Hydrogenolysis
2365:
2360:
2355:
2350:
2345:
2340:
2335:
2330:
2325:
2320:
2318:Étard reaction
2315:
2310:
2305:
2300:
2295:
2290:
2285:
2280:
2275:
2270:
2265:
2260:
2255:
2250:
2245:
2240:
2235:
2230:
2225:
2223:Bosch reaction
2220:
2215:
2210:
2205:
2200:
2195:
2190:
2185:
2180:
2175:
2170:
2165:
2160:
2155:
2150:
2145:
2140:
2134:
2132:
2128:Organic redox
2124:
2123:
2121:
2120:
2115:
2110:
2105:
2100:
2095:
2090:
2085:
2080:
2075:
2070:
2065:
2060:
2055:
2049:
2047:
2041:
2040:
2038:
2037:
2032:
2027:
2022:
2017:
2012:
2007:
2002:
1997:
1992:
1987:
1982:
1977:
1972:
1967:
1962:
1960:Esterification
1957:
1952:
1947:
1942:
1937:
1931:
1929:
1921:
1920:
1917:
1916:
1914:
1913:
1908:
1903:
1898:
1893:
1888:
1883:
1878:
1873:
1868:
1863:
1858:
1853:
1848:
1843:
1838:
1833:
1828:
1823:
1818:
1813:
1807:
1805:
1801:
1800:
1798:
1797:
1792:
1787:
1782:
1777:
1772:
1767:
1761:
1759:
1750:
1749:
1744:
1739:
1737:Wurtz reaction
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:
1607:Prins reaction
1604:
1599:
1594:
1589:
1584:
1579:
1574:
1569:
1564:
1559:
1554:
1549:
1544:
1539:
1534:
1529:
1524:
1519:
1514:
1509:
1504:
1499:
1494:
1489:
1484:
1479:
1474:
1469:
1464:
1459:
1454:
1449:
1444:
1439:
1434:
1429:
1424:
1422:Hydrocyanation
1419:
1414:
1409:
1404:
1399:
1394:
1392:Henry reaction
1389:
1384:
1379:
1374:
1369:
1364:
1359:
1354:
1349:
1344:
1339:
1334:
1329:
1324:
1319:
1314:
1309:
1304:
1299:
1294:
1289:
1284:
1279:
1274:
1269:
1264:
1259:
1254:
1249:
1244:
1239:
1234:
1229:
1224:
1219:
1214:
1209:
1204:
1199:
1194:
1189:
1184:
1179:
1174:
1169:
1164:
1159:
1154:
1149:
1144:
1139:
1134:
1129:
1124:
1119:
1114:
1109:
1104:
1099:
1094:
1092:Aldol reaction
1089:
1084:
1079:
1073:
1071:
1066:Carbon-carbon
1063:
1062:
1057:
1051:
1050:
1045:
1043:Zaitsev's rule
1040:
1035:
1030:
1025:
1020:
1015:
1010:
1005:
1000:
995:
990:
988:Steric effects
985:
980:
975:
970:
965:
960:
955:
950:
945:
940:
935:
930:
925:
920:
915:
910:
905:
900:
895:
890:
885:
880:
875:
870:
865:
860:
855:
850:
845:
840:
835:
830:
825:
820:
815:
810:
805:
800:
795:
790:
785:
780:
775:
770:
765:
760:
755:
750:
745:
740:
735:
730:
725:
720:
715:
710:
705:
700:
695:
690:
685:
680:
675:
669:
666:
665:
663:
662:
657:
652:
647:
642:
640:Redox reaction
637:
632:
627:
625:Polymerization
622:
617:
611:
608:
607:
601:
599:
598:
591:
584:
576:
568:
567:
546:(4): 273–284.
526:
483:
457:
430:
407:
395:
383:
356:
347:
338:
333:
325:
315:
314:
312:
309:
308:
307:
302:
297:
292:
285:
282:
239:
236:
235:
234:
214:
213:
187:
186:
171:
170:
142:
139:
130:
127:Stereomutation
52:stereospecific
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
3903:
3892:
3889:
3888:
3886:
3863:
3860:
3858:
3855:
3853:
3850:
3848:
3845:
3843:
3840:
3838:
3835:
3833:
3830:
3828:
3825:
3823:
3820:
3818:
3815:
3813:
3810:
3808:
3805:
3803:
3800:
3798:
3795:
3793:
3790:
3788:
3785:
3783:
3782:Herz reaction
3780:
3778:
3775:
3773:
3770:
3768:
3765:
3763:
3760:
3758:
3755:
3753:
3750:
3748:
3745:
3743:
3740:
3738:
3735:
3733:
3730:
3728:
3725:
3723:
3720:
3718:
3715:
3713:
3710:
3708:
3705:
3703:
3700:
3698:
3695:
3693:
3690:
3688:
3685:
3683:
3680:
3678:
3675:
3673:
3670:
3668:
3665:
3663:
3660:
3659:
3657:
3653:
3647:
3644:
3642:
3639:
3637:
3634:
3632:
3629:
3627:
3624:
3622:
3619:
3617:
3614:
3612:
3609:
3607:
3604:
3602:
3599:
3597:
3594:
3592:
3589:
3587:
3584:
3582:
3579:
3577:
3574:
3572:
3569:
3567:
3564:
3562:
3559:
3557:
3554:
3552:
3549:
3547:
3544:
3542:
3539:
3537:
3534:
3532:
3529:
3527:
3524:
3522:
3519:
3517:
3514:
3512:
3509:
3507:
3504:
3502:
3499:
3497:
3494:
3492:
3489:
3488:
3486:
3484:
3483:Cycloaddition
3480:
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:
3328:Isay reaction
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:
3223:Cycloaddition
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:
3129:
3126:
3125:
3123:
3121:
3118:Ring forming
3115:
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:
3018:Rupe reaction
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:
2896:
2894:
2891:
2889:
2886:
2884:
2881:
2879:
2876:
2874:
2871:
2869:
2866:
2864:
2861:
2859:
2856:
2854:
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:
2786:
2784:
2781:
2779:
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:
2666:
2664:
2661:
2659:
2656:
2654:
2651:
2649:
2646:
2644:
2641:
2640:
2638:
2636:
2630:
2624:
2621:
2619:
2616:
2614:
2611:
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:
2539:
2536:
2534:
2531:
2529:
2526:
2524:
2521:
2519:
2516:
2514:
2511:
2509:
2506:
2504:
2501:
2499:
2496:
2494:
2491:
2489:
2486:
2484:
2481:
2479:
2476:
2474:
2471:
2469:
2466:
2464:
2461:
2459:
2456:
2454:
2451:
2449:
2446:
2444:
2441:
2439:
2436:
2434:
2431:
2429:
2426:
2424:
2421:
2419:
2416:
2414:
2411:
2409:
2408:Ley oxidation
2406:
2404:
2401:
2399:
2396:
2394:
2391:
2389:
2386:
2384:
2381:
2379:
2376:
2374:
2373:Hydroxylation
2371:
2369:
2366:
2364:
2363:Hydrogenation
2361:
2359:
2356:
2354:
2351:
2349:
2346:
2344:
2341:
2339:
2336:
2334:
2331:
2329:
2326:
2324:
2321:
2319:
2316:
2314:
2311:
2309:
2306:
2304:
2301:
2299:
2298:DNA oxidation
2296:
2294:
2291:
2289:
2288:Deoxygenation
2286:
2284:
2281:
2279:
2276:
2274:
2271:
2269:
2266:
2264:
2261:
2259:
2256:
2254:
2251:
2249:
2246:
2244:
2241:
2239:
2236:
2234:
2231:
2229:
2226:
2224:
2221:
2219:
2216:
2214:
2211:
2209:
2206:
2204:
2201:
2199:
2196:
2194:
2191:
2189:
2186:
2184:
2181:
2179:
2178:Aromatization
2176:
2174:
2171:
2169:
2166:
2164:
2161:
2159:
2156:
2154:
2151:
2149:
2146:
2144:
2141:
2139:
2136:
2135:
2133:
2131:
2125:
2119:
2116:
2114:
2111:
2109:
2106:
2104:
2101:
2099:
2096:
2094:
2091:
2089:
2086:
2084:
2081:
2079:
2076:
2074:
2071:
2069:
2066:
2064:
2061:
2059:
2056:
2054:
2051:
2050:
2048:
2042:
2036:
2033:
2031:
2028:
2026:
2023:
2021:
2018:
2016:
2015:Reed reaction
2013:
2011:
2008:
2006:
2003:
2001:
1998:
1996:
1993:
1991:
1988:
1986:
1983:
1981:
1978:
1976:
1973:
1971:
1968:
1966:
1963:
1961:
1958:
1956:
1953:
1951:
1948:
1946:
1943:
1941:
1938:
1936:
1933:
1932:
1930:
1926:bond forming
1922:
1912:
1909:
1907:
1904:
1902:
1899:
1897:
1894:
1892:
1889:
1887:
1884:
1882:
1879:
1877:
1874:
1872:
1869:
1867:
1864:
1862:
1859:
1857:
1854:
1852:
1849:
1847:
1844:
1842:
1839:
1837:
1834:
1832:
1831:Cope reaction
1829:
1827:
1824:
1822:
1819:
1817:
1814:
1812:
1809:
1808:
1806:
1802:
1796:
1793:
1791:
1788:
1786:
1783:
1781:
1778:
1776:
1773:
1771:
1768:
1766:
1763:
1762:
1760:
1758:
1754:
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:
1563:
1560:
1558:
1555:
1553:
1550:
1548:
1545:
1543:
1542:Nef synthesis
1540:
1538:
1535:
1533:
1530:
1528:
1525:
1523:
1520:
1518:
1517:Methylenation
1515:
1513:
1510:
1508:
1505:
1503:
1500:
1498:
1495:
1493:
1490:
1488:
1485:
1483:
1480:
1478:
1475:
1473:
1470:
1468:
1465:
1463:
1460:
1458:
1455:
1453:
1450:
1448:
1445:
1443:
1440:
1438:
1435:
1433:
1430:
1428:
1425:
1423:
1420:
1418:
1415:
1413:
1410:
1408:
1405:
1403:
1400:
1398:
1395:
1393:
1390:
1388:
1387:Heck reaction
1385:
1383:
1380:
1378:
1375:
1373:
1370:
1368:
1365:
1363:
1360:
1358:
1355:
1353:
1350:
1348:
1345:
1343:
1340:
1338:
1335:
1333:
1330:
1328:
1325:
1323:
1320:
1318:
1315:
1313:
1310:
1308:
1305:
1303:
1300:
1298:
1295:
1293:
1290:
1288:
1285:
1283:
1280:
1278:
1275:
1273:
1270:
1268:
1265:
1263:
1260:
1258:
1255:
1253:
1250:
1248:
1245:
1243:
1240:
1238:
1235:
1233:
1230:
1228:
1225:
1223:
1220:
1218:
1215:
1213:
1210:
1208:
1205:
1203:
1200:
1198:
1195:
1193:
1190:
1188:
1185:
1183:
1180:
1178:
1175:
1173:
1170:
1168:
1165:
1163:
1160:
1158:
1155:
1153:
1150:
1148:
1145:
1143:
1140:
1138:
1135:
1133:
1130:
1128:
1125:
1123:
1120:
1118:
1115:
1113:
1110:
1108:
1105:
1103:
1100:
1098:
1095:
1093:
1090:
1088:
1085:
1083:
1080:
1078:
1075:
1074:
1072:
1068:bond forming
1064:
1060:
1055:
1049:
1046:
1044:
1041:
1039:
1036:
1034:
1033:Y-aromaticity
1031:
1029:
1026:
1024:
1021:
1019:
1018:Walsh diagram
1016:
1014:
1011:
1009:
1006:
1004:
1003:Taft equation
1001:
999:
996:
994:
991:
989:
986:
984:
981:
979:
976:
974:
973:Σ-aromaticity
971:
969:
966:
964:
961:
959:
956:
954:
951:
949:
946:
944:
941:
939:
936:
934:
931:
929:
926:
924:
921:
919:
916:
914:
911:
909:
906:
904:
901:
899:
898:Marcus theory
896:
894:
891:
889:
886:
884:
881:
879:
876:
874:
873:Hückel's rule
871:
869:
866:
864:
861:
859:
856:
854:
851:
849:
846:
844:
841:
839:
836:
834:
831:
829:
828:Evelyn effect
826:
824:
821:
819:
816:
814:
811:
809:
808:Electron-rich
806:
804:
801:
799:
796:
794:
791:
789:
786:
784:
781:
779:
776:
774:
771:
769:
766:
764:
761:
759:
756:
754:
751:
749:
746:
744:
741:
739:
736:
734:
731:
729:
726:
724:
723:Bema Hapothle
721:
719:
716:
714:
711:
709:
706:
704:
701:
699:
696:
694:
691:
689:
686:
684:
681:
679:
676:
674:
671:
670:
667:
661:
658:
656:
653:
651:
648:
646:
643:
641:
638:
636:
633:
631:
628:
626:
623:
621:
618:
616:
613:
612:
609:
605:
597:
592:
590:
585:
583:
578:
577:
574:
563:
559:
554:
549:
545:
541:
537:
530:
527:
522:
518:
514:
510:
506:
502:
498:
494:
487:
484:
481:
477:
473:
470:
466:
461:
458:
455:
451:
447:
443:
439:
434:
431:
428:
424:
420:
416:
411:
408:
405:
399:
396:
393:
387:
384:
381:
377:
373:
369:
365:
360:
357:
351:
348:
342:
339:
329:
326:
320:
317:
310:
306:
303:
301:
298:
296:
293:
291:
288:
287:
283:
281:
279:
274:
272:
271:
266:
262:
258:
254:
253:
248:
244:
237:
232:
228:
227:
226:
224:
219:
211:
207:
206:
205:
203:
199:
196:
192:
184:
180:
179:
178:
175:
168:
164:
163:
162:
160:
156:
152:
148:
140:
138:
136:
128:
124:
121:
119:
115:
113:
108:
104:
99:
97:
93:
89:
85:
81:
76:
73:
69:
65:
61:
57:
53:
50:during a non-
49:
48:stereoisomers
45:
41:
37:
33:
19:
2823:Ene reaction
2183:Autoxidation
2044:Degradation
1935:Azo coupling
1712:Ugi reaction
1312:Ene reaction
1112:Alkynylation
963:Polyfluorene
958:Polar effect
823:Electrophile
738:Bredt's rule
708:Baird's rule
678:Alpha effect
649:
543:
539:
529:
496:
492:
486:
471:
464:
460:
445:
437:
433:
421:: 3428-3436
418:
414:
410:
398:
386:
371:
363:
359:
350:
341:
328:
319:
275:
268:
250:
241:
215:
188:
172:
154:
150:
144:
126:
125:
122:
117:
116:
107:diastereomer
102:
100:
79:
77:
56:stereocenter
35:
29:
1322:Ethenolysis
968:Ring strain
938:Nucleophile
763:Clar's rule
703:Aromaticity
257:pinoresinol
243:Pinoresinol
218:stereogenic
174:Cram's rule
3606:Ozonolysis
3133:Annulation
2483:Ozonolysis
602:Topics in
84:enantiomer
3120:reactions
2635:reactions
2130:reactions
2046:reactions
1928:reactions
1070:reactions
562:195313754
32:chemistry
3885:Category
1013:Vinylogy
683:Annulene
630:Reagents
521:41957412
284:See also
141:Examples
44:reactant
673:A value
513:8994027
493:Science
223:t-butyl
216:With a
195:achiral
66:in the
560:
519:
511:
88:enzyme
60:steric
558:S2CID
517:S2CID
474:, 48
259:from
151:trans
509:PMID
472:2009
446:2005
419:2005
404:Link
392:Link
372:1973
189:The
62:and
548:doi
501:doi
497:275
476:doi
450:doi
423:doi
376:doi
155:cis
78:An
30:In
3887::
556:.
544:53
542:.
538:.
515:.
507:.
495:.
444:,
370:;
114:.
101:A
34:,
595:e
588:t
581:v
564:.
550::
523:.
503::
478::
452::
425::
378::
334:N
131:N
20:)
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