267:
220:
172:
199:
156:
87:, 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.
165:
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
98:
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
126:), 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).
312:(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.
209:
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
63:
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.
112:
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.
1520:
99:
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
266:
3735:
480:
Davin LB, Wang HB, Crowell AL, et al. (1997). "Stereoselective bimolecular phenoxy radical coupling by an auxiliary (dirigent) protein without an active center".
75:
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
189:
substrate is transformed into an optically active epoxyalcohol. In the case of chiral allylic alcohols, kinetic resolution results. Another example is
219:
2851:
2796:
3564:
171:
2906:
123:
3056:
1690:
3785:
3559:
1385:
109:
can be considered an opposite of stereospecificity, when the reaction of two different stereoisomers yield a single product stereoisomer.
2661:
582:
3231:
2431:
1175:
3396:
3326:
3306:
2801:
1968:
1430:
1849:
1405:
618:
3151:
198:
3629:
3579:
1983:
3086:
3725:
3534:
3191:
3171:
3131:
1938:
881:
3720:
3650:
3549:
3206:
3061:
2691:
2536:
2146:
1773:
1550:
190:
3800:
3584:
2896:
2386:
2061:
2606:
3795:
3509:
3371:
3161:
3126:
155:
3685:
3624:
3156:
3071:
3041:
3021:
2886:
2881:
2256:
2181:
1824:
1778:
1645:
906:
3790:
3750:
3700:
3376:
3176:
2926:
2856:
1345:
916:
525:"An Enantiocomplementary Dirigent Protein for the Enantioselective Laccase-Catalyzed Oxidative Coupling of Phenols"
2991:
1884:
1605:
3544:
3386:
3256:
3251:
3066:
2541:
2451:
2041:
1973:
1864:
1440:
1195:
1120:
575:
3301:
404:
Diastereoselective
Friedel-Crafts Cyclization Reactions to 2-Substituted 1-Phenyl-1,2,3,4-tetrahydronaphthalenes
47:
or during a non-stereospecific transformation of a pre-existing one. The selectivity arises from differences in
3830:
3715:
3614:
3554:
3201:
2996:
2956:
2931:
2841:
2301:
1335:
1265:
901:
831:
2421:
3820:
3406:
3296:
2916:
2641:
2426:
2371:
2216:
2176:
2008:
1763:
1480:
1330:
3780:
3341:
2786:
59:
leading to the different products. Stereoselectivity can vary in degree but it can never be total since the
3815:
3730:
3705:
3680:
3665:
3589:
3504:
3401:
3361:
3226:
3181:
2946:
2491:
2476:
2341:
2131:
1799:
1555:
1235:
1210:
1180:
771:
343:
Eliel, E.L. & Willen S.H., "Stereochemistry of
Organic Compounds", John Wiley & Sons, 2008 pp 1209.
3765:
3710:
3655:
3366:
3286:
3186:
2901:
2866:
2711:
2601:
2316:
2311:
2136:
2096:
1993:
1804:
1768:
1620:
1610:
1465:
1325:
1185:
1135:
1130:
1105:
1065:
1011:
776:
766:
741:
118:
is a general term for the conversion of one stereoisomer into another. For example, racemization (as in S
3740:
3441:
3246:
2681:
2566:
2246:
2221:
2161:
2018:
1753:
1460:
1240:
1205:
1110:
801:
736:
568:
3031:
1295:
3840:
3745:
3599:
3479:
3451:
3421:
3336:
3266:
3221:
3196:
3116:
3016:
2976:
2671:
2291:
2281:
2206:
1730:
1590:
1585:
1565:
1250:
1047:
1026:
986:
911:
731:
3879:
3805:
3695:
3675:
3539:
3381:
3291:
3261:
3241:
3136:
3091:
2921:
2831:
2761:
2646:
2636:
2466:
2023:
1963:
1928:
1735:
1715:
1675:
1450:
1320:
1285:
1245:
996:
836:
826:
756:
166:
with a thiazole to form the (S,S) diastereomer but only a small amount of the (S,R) diastereomer:
3271:
427:
3775:
3634:
3484:
3426:
3351:
3331:
3051:
3001:
2861:
2826:
2766:
2696:
2251:
1998:
1978:
1710:
1630:
1525:
1485:
1455:
1390:
1275:
1260:
1170:
1160:
821:
746:
701:
278:
1036:
3514:
3236:
2986:
2966:
2941:
2891:
2806:
2781:
2736:
2706:
2686:
2656:
2621:
2576:
2551:
2526:
2411:
2336:
2116:
1809:
1745:
1545:
1270:
1190:
876:
851:
628:
623:
3850:
3436:
3391:
3106:
3076:
3046:
2981:
2961:
2876:
2871:
2836:
2791:
2776:
2771:
2751:
2741:
2676:
2666:
2596:
2546:
2066:
1869:
1445:
1400:
1230:
1220:
966:
891:
686:
648:
457:
183:
179:
150:
are also classified as diastereomers, this reaction would also be called diastereoselective.
100:
896:
3619:
3569:
3519:
3499:
3489:
3346:
3321:
3036:
3026:
2911:
2726:
2721:
2651:
2436:
2236:
2196:
2126:
2091:
2046:
2013:
1879:
1854:
1834:
1655:
1615:
1575:
1540:
1470:
1225:
1095:
1070:
608:
258:
240:
193:. In the example below the achiral alkene yields only one of the possible 4 stereoisomers.
8:
3825:
3810:
3456:
3431:
3416:
3411:
3141:
3096:
3081:
2971:
2951:
2846:
2731:
2716:
2561:
2506:
2496:
2461:
2226:
2101:
2076:
1988:
1844:
1829:
1814:
1635:
1580:
1350:
1200:
1145:
1016:
931:
791:
716:
135:
80:
3835:
2486:
1670:
861:
3574:
3524:
3494:
3356:
3146:
2936:
2821:
2756:
2746:
2511:
2441:
2406:
2401:
2381:
2376:
2321:
2231:
2081:
1943:
1933:
1839:
1625:
1570:
1500:
1420:
1315:
1215:
1150:
1075:
921:
786:
721:
706:
546:
505:
84:
56:
52:
523:
Pickel B, Constantin M-A, Pfannsteil J, Conrad J, Beifuss U, Schaffer A (March 2007).
3311:
2631:
2516:
2481:
2446:
2391:
2346:
2261:
2241:
2191:
2186:
2156:
2141:
2051:
1958:
1894:
1859:
1685:
1560:
1435:
1360:
1340:
1255:
1090:
1085:
1031:
941:
846:
806:
761:
643:
603:
550:
497:
430:
356:
283:
249:
60:
40:
28:
2306:
509:
3845:
3690:
3660:
3604:
3529:
3461:
3216:
3166:
3011:
2816:
2591:
2586:
2531:
2521:
2296:
2106:
2086:
2056:
1953:
1889:
1874:
1705:
1660:
1650:
1640:
1535:
1515:
1510:
1495:
1490:
1370:
1365:
1305:
1290:
1280:
1125:
1115:
981:
971:
871:
866:
841:
781:
633:
592:
536:
489:
464:
438:
411:
364:
293:
288:
253:
235:
147:
961:
3755:
3446:
3281:
3276:
2571:
2556:
2501:
2456:
2416:
2366:
2331:
2326:
2271:
2266:
2201:
2151:
2071:
1899:
1783:
1758:
1720:
1695:
1680:
1665:
1600:
1475:
1425:
1415:
1395:
1355:
1165:
1155:
1140:
936:
856:
726:
696:
681:
676:
493:
186:
122:
1 reactions), epimerization (as in interconversion of D-glucose and D-mannose in
36:
244:. This protein has been found to direct the stereoselective biosynthesis of (+)-
3760:
3670:
3609:
2701:
2611:
2581:
2356:
2211:
1948:
1725:
1595:
1410:
1380:
1080:
976:
751:
613:
392:
380:
162:
48:
560:
541:
524:
353:
Effects of base strength and size upon in base-promoted elimination reactions.
3873:
3770:
3471:
3316:
3211:
3006:
2396:
2361:
2351:
2286:
2276:
2166:
2003:
1819:
1530:
1505:
1375:
1021:
1006:
991:
886:
816:
796:
711:
16:
Ability of a chemical reaction to produce an unequal mixture of stereoisomers
325:
1 reaction destroys a pre-existing stereocenter, and then creates a new one.
2811:
2171:
1923:
1700:
1300:
1100:
951:
946:
811:
666:
468:
95:
44:
501:
415:
1310:
956:
926:
691:
245:
231:
206:
368:
3594:
3121:
2471:
355:
Richard A. Bartsch, Gerald M. Pruss, Bruce A. Bushaw, Karl E. Wiegers
72:
442:
379:
Organic
Syntheses, Coll. Vol. 10, p.140 (2004); Vol. 77, p.78 (2000).
391:
Organic
Syntheses, Coll. Vol. 10, p.603 (2004); Vol. 79, p.93 (2002).
20:
522:
1001:
671:
334:
Or fewer than all possible relative stereochemistries are obtained.
32:
79:
or a chiral reagent. The degree of selectivity is measured by the
661:
211:
262:, which directs enantioselective synthesis of (−)-pinoresinol.
76:
182:
is an example of an enantioselective process, in which an
429:
Friedrich Mühlthau, Oliver
Schuster, and Thorsten Bach
454:
Stereoselective
Reactions with Stabilized Carbocations
214:
group resulting in high facial diastereoselectivity:
3736:
Erlenmeyer–Plöchl azlactone and amino-acid synthesis
252:monomers. Recently, a second, enantiocomplementary
2797:Divinylcyclopropane-cycloheptadiene rearrangement
3871:
479:
590:
238:. The first dirigent protein was discovered in
226:
3057:Thermal rearrangement of aromatic hydrocarbons
1691:Thermal rearrangement of aromatic hydrocarbons
134:An example of modest stereoselectivity is the
3786:Lectka enantioselective beta-lactam synthesis
1046:
576:
3565:Inverse electron-demand Diels–Alder reaction
1386:Heterogeneous metal catalyzed cross-coupling
406:Friedrich Mühlthau, Thorsten Bach Synthesis
2907:Lobry de Bruyn–Van Ekenstein transformation
124:Lobry de Bruyn–Van Ekenstein transformation
583:
569:
3397:Petrenko-Kritschenko piperidone synthesis
2852:Fritsch–Buttenberg–Wiechell rearrangement
540:
234:biosynthesis involved a protein called a
3560:Intramolecular Diels–Alder cycloaddition
299:
3872:
3580:Metal-centered cycloaddition reactions
3232:Debus–Radziszewski imidazole synthesis
1176:Bodroux–Chichibabin aldehyde synthesis
456:Pier Giorgio Cozzi and Fides Benfatti
3726:Diazoalkane 1,3-dipolar cycloaddition
3630:Vinylcyclopropane (5+2) cycloaddition
3535:Diazoalkane 1,3-dipolar cycloaddition
3307:Hurd–Mori 1,2,3-thiadiazole synthesis
2802:Dowd–Beckwith ring-expansion reaction
1969:Hurd–Mori 1,2,3-thiadiazole synthesis
1045:
882:LFER solvent coefficients (data page)
564:
2537:Sharpless asymmetric dihydroxylation
1774:Methoxymethylenetriphenylphosphorane
191:Sharpless asymmetric dihydroxylation
2662:Allen–Millar–Trippett rearrangement
13:
3801:Nitrone-olefin (3+2) cycloaddition
3796:Niementowski quinazoline synthesis
3585:Nitrone-olefin (3+2) cycloaddition
3510:Azide-alkyne Huisgen cycloaddition
3372:Niementowski quinazoline synthesis
3127:Azide-alkyne Huisgen cycloaddition
2432:Meerwein–Ponndorf–Verley reduction
1984:Leimgruber–Batcho indole synthesis
14:
3891:
3625:Trimethylenemethane cycloaddition
3327:Johnson–Corey–Chaykovsky reaction
3192:Cadogan–Sundberg indole synthesis
3172:Bohlmann–Rahtz pyridine synthesis
3132:Baeyer–Emmerling indole synthesis
1939:Cadogan–Sundberg indole synthesis
1431:Johnson–Corey–Chaykovsky reaction
138:of 2-iodobutane which yields 60%
3721:Cook–Heilbron thiazole synthesis
3550:Hexadehydro Diels–Alder reaction
3377:Niementowski quinoline synthesis
3207:Cook–Heilbron thiazole synthesis
3152:Bischler–Möhlau indole synthesis
3062:Tiffeneau–Demjanov rearrangement
2692:Baker–Venkataraman rearrangement
1850:Horner–Wadsworth–Emmons reaction
1521:Mizoroki-Heck vs. Reductive Heck
1406:Horner–Wadsworth–Emmons reaction
917:Neighbouring group participation
265:
218:
197:
170:
154:
3257:Fiesselmann thiophene synthesis
3087:Westphalen–Lettré rearrangement
3067:Vinylcyclopropane rearrangement
2897:Kornblum–DeLaMare rearrangement
2542:Epoxidation of allylic alcohols
2452:Noyori asymmetric hydrogenation
2387:Kornblum–DeLaMare rearrangement
2062:Gallagher–Hollander degradation
516:
473:
447:
3716:Chichibabin pyridine synthesis
3202:Chichibabin pyridine synthesis
3162:Blum–Ittah aziridine synthesis
2997:Ring expansion and contraction
1266:Cross dehydrogenative coupling
420:
397:
385:
373:
346:
337:
328:
315:
306:
1:
3686:Bischler–Napieralski reaction
3644:Heterocycle forming reactions
3297:Hemetsberger indole synthesis
3157:Bischler–Napieralski reaction
3072:Wagner–Meerwein rearrangement
3042:Sommelet–Hauser rearrangement
3022:Seyferth–Gilbert homologation
2887:Ireland–Claisen rearrangement
2882:Hofmann–Martius rearrangement
2642:2,3-sigmatropic rearrangement
2257:Corey–Winter olefin synthesis
2182:Barton–McCombie deoxygenation
1825:Corey–Winter olefin synthesis
1779:Seyferth–Gilbert homologation
1646:Seyferth–Gilbert homologation
94:reaction is one in which one
71:reaction is one in which one
3791:Lehmstedt–Tanasescu reaction
3751:Gabriel–Colman rearrangement
3706:Bucherer carbazole synthesis
3701:Borsche–Drechsel cyclization
3681:Bernthsen acridine synthesis
3666:Bamberger triazine synthesis
3651:Algar–Flynn–Oyamada reaction
3362:Nazarov cyclization reaction
3227:De Kimpe aziridine synthesis
3182:Bucherer carbazole synthesis
3177:Borsche–Drechsel cyclization
2947:Nazarov cyclization reaction
2927:Meyer–Schuster rearrangement
2857:Gabriel–Colman rearrangement
2607:Wolffenstein–Böters reaction
2492:Reduction of nitro compounds
2342:Grundmann aldehyde synthesis
2147:Algar–Flynn–Oyamada reaction
1556:Olefin conversion technology
1551:Nozaki–Hiyama–Kishi reaction
1346:Gabriel–Colman rearrangement
1236:Claisen-Schmidt condensation
1181:Bouveault aldehyde synthesis
494:10.1126/science.275.5298.362
227:Stereoselective biosynthesis
35:forms an unequal mixture of
7:
3766:Hantzsch pyridine synthesis
3545:Enone–alkene cycloadditions
3367:Nenitzescu indole synthesis
3287:Hantzsch pyridine synthesis
3252:Ferrario–Ackermann reaction
2902:Kowalski ester homologation
2867:Halogen dance rearrangement
2712:Benzilic acid rearrangement
2137:Akabori amino-acid reaction
2097:Von Braun amide degradation
2042:Barbier–Wieland degradation
1994:Nenitzescu indole synthesis
1974:Kharasch–Sosnovsky reaction
1865:Julia–Kocienski olefination
1769:Kowalski ester homologation
1466:Kowalski ester homologation
1441:Julia–Kocienski olefination
1196:Cadiot–Chodkiewicz coupling
1121:Aza-Baylis–Hillman reaction
1066:Acetoacetic ester synthesis
777:Dynamic binding (chemistry)
767:Conrotatory and disrotatory
742:Charge remote fragmentation
272:
129:
10:
3896:
3831:Robinson–Gabriel synthesis
3781:Kröhnke pyridine synthesis
3615:Retro-Diels–Alder reaction
3555:Imine Diels–Alder reaction
3342:Kröhnke pyridine synthesis
2957:Newman–Kwart rearrangement
2932:Mislow–Evans rearrangement
2842:Fischer–Hepp rearrangement
2787:Di-π-methane rearrangement
2567:Stephen aldehyde synthesis
2302:Eschweiler–Clarke reaction
2019:Williamson ether synthesis
1336:Fujiwara–Moritani reaction
1241:Combes quinoline synthesis
1206:Carbonyl olefin metathesis
907:More O'Ferrall–Jencks plot
832:Grunwald–Winstein equation
802:Electron-withdrawing group
737:Catalytic resonance theory
83:. An important variant is
3841:Urech hydantoin synthesis
3821:Pomeranz–Fritsch reaction
3746:Fischer oxazole synthesis
3643:
3480:1,3-Dipolar cycloaddition
3470:
3452:Urech hydantoin synthesis
3422:Reissert indole synthesis
3407:Pomeranz–Fritsch reaction
3337:Knorr quinoline synthesis
3267:Fischer oxazole synthesis
3197:Camps quinoline synthesis
3117:1,3-Dipolar cycloaddition
3105:
3017:Semipinacol rearrangement
2992:Ramberg–Bäcklund reaction
2977:Piancatelli rearrangement
2917:McFadyen–Stevens reaction
2672:Alpha-ketol rearrangement
2620:
2427:McFadyen–Stevens reaction
2372:Kiliani–Fischer synthesis
2292:Elbs persulfate oxidation
2217:Bouveault–Blanc reduction
2177:Baeyer–Villiger oxidation
2115:
2032:
2009:Schotten–Baumann reaction
1912:
1885:Ramberg–Bäcklund reaction
1792:
1764:Kiliani–Fischer synthesis
1744:
1606:Ramberg–Bäcklund reaction
1591:Pinacol coupling reaction
1586:Piancatelli rearrangement
1481:Liebeskind–Srogl coupling
1331:Fujimoto–Belleau reaction
1054:
1048:List of organic reactions
912:Negative hyperconjugation
657:
599:
542:10.1007/s10086-007-0892-x
437:, 127 (26), pp 9348–9349
3816:Pictet–Spengler reaction
3731:Einhorn–Brunner reaction
3696:Boger pyridine synthesis
3590:Oxo-Diels–Alder reaction
3505:Aza-Diels–Alder reaction
3402:Pictet–Spengler reaction
3302:Hofmann–Löffler reaction
3292:Hegedus indole synthesis
3262:Fischer indole synthesis
3137:Bartoli indole synthesis
3092:Willgerodt rearrangement
2922:McLafferty rearrangement
2832:Ferrier carbocyclization
2647:2,3-Wittig rearrangement
2637:1,2-Wittig rearrangement
2477:Parikh–Doering oxidation
2467:Oxygen rebound mechanism
2132:Adkins–Peterson reaction
2024:Yamaguchi esterification
1964:Hegedus indole synthesis
1929:Bartoli indole synthesis
1800:Bamford–Stevens reaction
1716:Weinreb ketone synthesis
1676:Stork enamine alkylation
1451:Knoevenagel condensation
1321:Ferrier carbocyclization
1211:Castro–Stephens coupling
837:Hammett acidity function
827:Free-energy relationship
772:Curtin–Hammett principle
757:Conformational isomerism
146:-2-butene. Since alkene
3776:Knorr pyrrole synthesis
3711:Bucherer–Bergs reaction
3656:Allan–Robinson reaction
3635:Wagner-Jauregg reaction
3427:Ring-closing metathesis
3352:Larock indole synthesis
3332:Knorr pyrrole synthesis
3187:Bucherer–Bergs reaction
3052:Stieglitz rearrangement
3032:Skattebøl rearrangement
3002:Ring-closing metathesis
2862:Group transfer reaction
2827:Favorskii rearrangement
2767:Cornforth rearrangement
2697:Bamberger rearrangement
2602:Wolff–Kishner reduction
2422:Markó–Lam deoxygenation
2317:Fleming–Tamao oxidation
2312:Fischer–Tropsch process
1999:Oxymercuration reaction
1979:Knorr pyrrole synthesis
1805:Barton–Kellogg reaction
1711:Wagner-Jauregg reaction
1631:Ring-closing metathesis
1621:Reimer–Tiemann reaction
1611:Rauhut–Currier reaction
1526:Nef isocyanide reaction
1486:Malonic ester synthesis
1456:Knorr pyrrole synthesis
1391:High dilution principle
1326:Friedel–Crafts reaction
1261:Cross-coupling reaction
1186:Bucherer–Bergs reaction
1171:Blanc chloromethylation
1161:Blaise ketone synthesis
1136:Baylis–Hillman reaction
1131:Barton–Kellogg reaction
1106:Allan–Robinson reaction
1012:Woodward–Hoffmann rules
747:Charge-transfer complex
279:Dynamic stereochemistry
3741:Feist–Benary synthesis
3515:Bradsher cycloaddition
3485:4+4 Photocycloaddition
3442:Simmons–Smith reaction
3387:Paternò–Büchi reaction
3247:Feist–Benary synthesis
3237:Dieckmann condensation
2987:Pummerer rearrangement
2967:Oxy-Cope rearrangement
2942:Myers allene synthesis
2892:Jacobsen rearrangement
2807:Electrocyclic reaction
2782:Demjanov rearrangement
2737:Buchner ring expansion
2707:Beckmann rearrangement
2687:Aza-Cope rearrangement
2682:Arndt–Eistert reaction
2657:Alkyne zipper reaction
2577:Transfer hydrogenation
2552:Sharpless oxyamination
2527:Selenoxide elimination
2412:Lombardo methylenation
2337:Griesbaum coozonolysis
2247:Corey–Itsuno reduction
2222:Boyland–Sims oxidation
2162:Angeli–Rimini reaction
1810:Boord olefin synthesis
1754:Arndt–Eistert reaction
1746:Homologation reactions
1546:Nitro-Mannich reaction
1461:Kolbe–Schmitt reaction
1271:Cross-coupling partner
1191:Buchner ring expansion
1111:Arndt–Eistert reaction
877:Kinetic isotope effect
624:Rearrangement reaction
469:10.1002/anie.200905235
3600:Pauson–Khand reaction
3437:Sharpless epoxidation
3392:Pechmann condensation
3272:Friedländer synthesis
3222:Davis–Beirut reaction
3077:Wallach rearrangement
3047:Stevens rearrangement
2982:Pinacol rearrangement
2962:Overman rearrangement
2877:Hofmann rearrangement
2872:Hayashi rearrangement
2837:Ferrier rearrangement
2792:Dimroth rearrangement
2777:Curtius rearrangement
2772:Criegee rearrangement
2752:Claisen rearrangement
2742:Carroll rearrangement
2677:Amadori rearrangement
2667:Allylic rearrangement
2547:Sharpless epoxidation
2282:Dess–Martin oxidation
2207:Bohn–Schmidt reaction
2067:Hofmann rearrangement
1870:Kauffmann olefination
1793:Olefination reactions
1731:Wurtz–Fittig reaction
1566:Palladium–NHC complex
1446:Kauffmann olefination
1401:Homologation reaction
1251:Corey–House synthesis
1231:Claisen rearrangement
1027:Yukawa–Tsuno equation
987:Swain–Lupton equation
967:Spherical aromaticity
902:Möbius–Hückel concept
687:Aromatic ring current
649:Substitution reaction
458:Angew. Chem. Int. Ed.
416:10.1055/s-2005-918482
363:; 95(10); 3405-3407.
180:Sharpless epoxidation
101:diastereomeric excess
27:is the property of a
3806:Paal–Knorr synthesis
3676:Barton–Zard reaction
3620:Staudinger synthesis
3570:Ketene cycloaddition
3540:Diels–Alder reaction
3520:Cheletropic reaction
3500:Alkyne trimerisation
3382:Paal–Knorr synthesis
3347:Kulinkovich reaction
3322:Jacobsen epoxidation
3242:Diels–Alder reaction
3037:Smiles rearrangement
3027:Sigmatropic reaction
2912:Lossen rearrangement
2762:Corey–Fuchs reaction
2727:Boekelheide reaction
2722:Bergmann degradation
2652:Achmatowicz reaction
2437:Methionine sulfoxide
2237:Clemmensen reduction
2197:Bergmann degradation
2127:Acyloin condensation
2092:Strecker degradation
2047:Bergmann degradation
2014:Ullmann condensation
1880:Peterson olefination
1855:Hydrazone iodination
1835:Elimination reaction
1736:Zincke–Suhl reaction
1656:Sonogashira coupling
1616:Reformatsky reaction
1576:Peterson olefination
1541:Nierenstein reaction
1471:Kulinkovich reaction
1286:Diels–Alder reaction
1246:Corey–Fuchs reaction
1226:Claisen condensation
1096:Alkyne trimerisation
1071:Acyloin condensation
1037:Σ-bishomoaromaticity
997:Thorpe–Ingold effect
609:Elimination reaction
300:Notes and references
259:Arabidopsis thaliana
241:Forsythia intermedia
57:mechanistic pathways
3826:Prilezhaev reaction
3811:Pellizzari reaction
3490:(4+3) cycloaddition
3457:Van Leusen reaction
3432:Robinson annulation
3417:Pschorr cyclization
3412:Prilezhaev reaction
3142:Bergman cyclization
3097:Wolff rearrangement
3082:Weerman degradation
2972:Pericyclic reaction
2952:Neber rearrangement
2847:Fries rearrangement
2732:Brook rearrangement
2717:Bergman cyclization
2562:Staudinger reaction
2507:Rosenmund reduction
2497:Reductive amination
2462:Oppenauer oxidation
2252:Corey–Kim oxidation
2227:Cannizzaro reaction
2102:Weerman degradation
2077:Isosaccharinic acid
1989:Mukaiyama hydration
1845:Hofmann elimination
1830:Dehydrohalogenation
1815:Chugaev elimination
1636:Robinson annulation
1581:Pfitzinger reaction
1351:Gattermann reaction
1296:Wulff–Dötz reaction
1276:Dakin–West reaction
1201:Carbonyl allylation
1146:Bergman cyclization
932:Kennedy J. P. Orton
852:Hammond's postulate
822:Flippin–Lodge angle
792:Electromeric effect
717:Beta-silicon effect
702:Baker–Nathan effect
369:10.1021/ja00791a067
321:For instance, the S
136:dehydrohalogenation
81:enantiomeric excess
3575:McCormack reaction
3525:Conia-ene reaction
3357:Madelung synthesis
3147:Biginelli reaction
2937:Mumm rearrangement
2822:Favorskii reaction
2757:Cope rearrangement
2747:Chan rearrangement
2512:Rubottom oxidation
2442:Miyaura borylation
2407:Lipid peroxidation
2402:Lindgren oxidation
2382:Kornblum oxidation
2377:Kolbe electrolysis
2322:Fukuyama reduction
2232:Carbonyl reduction
2082:Marker degradation
1944:Diazonium compound
1934:Boudouard reaction
1913:Carbon-heteroatom
1840:Grieco elimination
1626:Rieche formylation
1571:Passerini reaction
1501:Meerwein arylation
1421:Hydroxymethylation
1316:Favorskii reaction
1216:Chan rearrangement
1151:Biginelli reaction
1076:Aldol condensation
922:2-Norbornyl cation
897:Möbius aromaticity
892:Markovnikov's rule
787:Effective molarity
732:Bürgi–Dunitz angle
722:Bicycloaromaticity
256:was identified in
142:-2-butene and 20%
92:diastereoselective
85:kinetic resolution
53:electronic effects
43:creation of a new
31:in which a single
3867:
3866:
3863:
3862:
3859:
3858:
3851:Wohl–Aue reaction
3495:6+4 Cycloaddition
3312:Iodolactonization
2632:1,2-rearrangement
2597:Wohl–Aue reaction
2517:Sabatier reaction
2482:Pinnick oxidation
2447:Mozingo reduction
2392:Leuckart reaction
2347:Haloform reaction
2262:Criegee oxidation
2242:Collins oxidation
2192:Benkeser reaction
2187:Bechamp reduction
2157:Andrussow process
2142:Alcohol oxidation
2052:Edman degradation
1959:Haloform reaction
1908:
1907:
1895:Takai olefination
1860:Julia olefination
1686:Takai olefination
1561:Olefin metathesis
1436:Julia olefination
1361:Grignard reaction
1341:Fukuyama coupling
1256:Coupling reaction
1221:Chan–Lam coupling
1091:Alkyne metathesis
1086:Alkane metathesis
942:Phosphaethynolate
847:George S. Hammond
807:Electronic effect
762:Conjugated system
644:Stereospecificity
639:Stereoselectivity
604:Addition reaction
593:organic reactions
529:Angewandte Chemie
443:10.1021/ja050626v
431:J. Am. Chem. Soc.
357:J. Am. Chem. Soc.
284:Torquoselectivity
250:coniferyl alcohol
148:geometric isomers
107:Stereoconvergence
61:activation energy
29:chemical reaction
25:stereoselectivity
3887:
3846:Wenker synthesis
3836:Stollé synthesis
3691:Bobbitt reaction
3661:Auwers synthesis
3605:Povarov reaction
3530:Cyclopropanation
3468:
3467:
3462:Wenker synthesis
3217:Darzens reaction
3167:Bobbitt reaction
3012:Schmidt reaction
2817:Enyne metathesis
2592:Whiting reaction
2587:Wharton reaction
2532:Shapiro reaction
2522:Sarett oxidation
2487:Prévost reaction
2297:Emde degradation
2107:Wohl degradation
2087:Ruff degradation
2057:Emde degradation
1954:Grignard reagent
1890:Shapiro reaction
1875:McMurry reaction
1742:
1741:
1706:Ullmann reaction
1671:Stollé synthesis
1661:Stetter reaction
1651:Shapiro reaction
1641:Sakurai reaction
1536:Negishi coupling
1516:Minisci reaction
1511:Michael reaction
1496:McMurry reaction
1491:Mannich reaction
1371:Hammick reaction
1366:Grignard reagent
1306:Enyne metathesis
1291:Doebner reaction
1281:Darzens reaction
1126:Barbier reaction
1116:Auwers synthesis
1043:
1042:
1017:Woodward's rules
982:Superaromaticity
972:Spiroaromaticity
872:Inductive effect
867:Hyperconjugation
842:Hammett equation
782:Edwards equation
634:Regioselectivity
585:
578:
571:
562:
561:
555:
554:
544:
520:
514:
513:
477:
471:
451:
445:
424:
418:
401:
395:
389:
383:
377:
371:
350:
344:
341:
335:
332:
326:
319:
313:
310:
294:Chemoselectivity
289:Regioselectivity
269:
254:dirigent protein
236:dirigent protein
222:
201:
174:
158:
69:enantioselective
3895:
3894:
3890:
3889:
3888:
3886:
3885:
3884:
3880:Stereochemistry
3870:
3869:
3868:
3855:
3756:Gewald reaction
3639:
3466:
3447:Skraup reaction
3282:Graham reaction
3277:Gewald reaction
3108:
3101:
2623:
2616:
2572:Swern oxidation
2557:Stahl oxidation
2502:Riley oxidation
2457:Omega oxidation
2417:Luche reduction
2367:Jones oxidation
2332:Glycol cleavage
2327:Ganem oxidation
2272:Davis oxidation
2267:Dakin oxidation
2202:Birch reduction
2152:Amide reduction
2118:
2111:
2072:Hooker reaction
2034:
2028:
1916:
1914:
1904:
1900:Wittig reaction
1788:
1784:Wittig reaction
1759:Hooker reaction
1740:
1721:Wittig reaction
1696:Thorpe reaction
1681:Suzuki reaction
1666:Stille reaction
1601:Quelet reaction
1476:Kumada coupling
1426:Ivanov reaction
1416:Hydrovinylation
1396:Hiyama coupling
1356:Glaser coupling
1166:Blaise reaction
1156:Bingel reaction
1141:Benary reaction
1058:
1056:
1050:
1041:
937:Passive binding
857:Homoaromaticity
707:Baldwin's rules
682:Antiaromaticity
677:Anomeric effect
653:
595:
589:
559:
558:
521:
517:
488:(5298): 362–6.
478:
474:
452:
448:
425:
421:
402:
398:
390:
386:
378:
374:
351:
347:
342:
338:
333:
329:
324:
320:
316:
311:
307:
302:
275:
229:
187:allylic alcohol
132:
121:
17:
12:
11:
5:
3893:
3883:
3882:
3865:
3864:
3861:
3860:
3857:
3856:
3854:
3853:
3848:
3843:
3838:
3833:
3828:
3823:
3818:
3813:
3808:
3803:
3798:
3793:
3788:
3783:
3778:
3773:
3768:
3763:
3761:Hantzsch ester
3758:
3753:
3748:
3743:
3738:
3733:
3728:
3723:
3718:
3713:
3708:
3703:
3698:
3693:
3688:
3683:
3678:
3673:
3671:Banert cascade
3668:
3663:
3658:
3653:
3647:
3645:
3641:
3640:
3638:
3637:
3632:
3627:
3622:
3617:
3612:
3610:Prato reaction
3607:
3602:
3597:
3592:
3587:
3582:
3577:
3572:
3567:
3562:
3557:
3552:
3547:
3542:
3537:
3532:
3527:
3522:
3517:
3512:
3507:
3502:
3497:
3492:
3487:
3482:
3476:
3474:
3465:
3464:
3459:
3454:
3449:
3444:
3439:
3434:
3429:
3424:
3419:
3414:
3409:
3404:
3399:
3394:
3389:
3384:
3379:
3374:
3369:
3364:
3359:
3354:
3349:
3344:
3339:
3334:
3329:
3324:
3319:
3314:
3309:
3304:
3299:
3294:
3289:
3284:
3279:
3274:
3269:
3264:
3259:
3254:
3249:
3244:
3239:
3234:
3229:
3224:
3219:
3214:
3209:
3204:
3199:
3194:
3189:
3184:
3179:
3174:
3169:
3164:
3159:
3154:
3149:
3144:
3139:
3134:
3129:
3124:
3119:
3113:
3111:
3103:
3102:
3100:
3099:
3094:
3089:
3084:
3079:
3074:
3069:
3064:
3059:
3054:
3049:
3044:
3039:
3034:
3029:
3024:
3019:
3014:
3009:
3004:
2999:
2994:
2989:
2984:
2979:
2974:
2969:
2964:
2959:
2954:
2949:
2944:
2939:
2934:
2929:
2924:
2919:
2914:
2909:
2904:
2899:
2894:
2889:
2884:
2879:
2874:
2869:
2864:
2859:
2854:
2849:
2844:
2839:
2834:
2829:
2824:
2819:
2814:
2809:
2804:
2799:
2794:
2789:
2784:
2779:
2774:
2769:
2764:
2759:
2754:
2749:
2744:
2739:
2734:
2729:
2724:
2719:
2714:
2709:
2704:
2702:Banert cascade
2699:
2694:
2689:
2684:
2679:
2674:
2669:
2664:
2659:
2654:
2649:
2644:
2639:
2634:
2628:
2626:
2622:Rearrangement
2618:
2617:
2615:
2614:
2612:Zinin reaction
2609:
2604:
2599:
2594:
2589:
2584:
2582:Wacker process
2579:
2574:
2569:
2564:
2559:
2554:
2549:
2544:
2539:
2534:
2529:
2524:
2519:
2514:
2509:
2504:
2499:
2494:
2489:
2484:
2479:
2474:
2469:
2464:
2459:
2454:
2449:
2444:
2439:
2434:
2429:
2424:
2419:
2414:
2409:
2404:
2399:
2394:
2389:
2384:
2379:
2374:
2369:
2364:
2359:
2357:Hydrogenolysis
2354:
2349:
2344:
2339:
2334:
2329:
2324:
2319:
2314:
2309:
2307:Étard reaction
2304:
2299:
2294:
2289:
2284:
2279:
2274:
2269:
2264:
2259:
2254:
2249:
2244:
2239:
2234:
2229:
2224:
2219:
2214:
2212:Bosch reaction
2209:
2204:
2199:
2194:
2189:
2184:
2179:
2174:
2169:
2164:
2159:
2154:
2149:
2144:
2139:
2134:
2129:
2123:
2121:
2117:Organic redox
2113:
2112:
2110:
2109:
2104:
2099:
2094:
2089:
2084:
2079:
2074:
2069:
2064:
2059:
2054:
2049:
2044:
2038:
2036:
2030:
2029:
2027:
2026:
2021:
2016:
2011:
2006:
2001:
1996:
1991:
1986:
1981:
1976:
1971:
1966:
1961:
1956:
1951:
1949:Esterification
1946:
1941:
1936:
1931:
1926:
1920:
1918:
1910:
1909:
1906:
1905:
1903:
1902:
1897:
1892:
1887:
1882:
1877:
1872:
1867:
1862:
1857:
1852:
1847:
1842:
1837:
1832:
1827:
1822:
1817:
1812:
1807:
1802:
1796:
1794:
1790:
1789:
1787:
1786:
1781:
1776:
1771:
1766:
1761:
1756:
1750:
1748:
1739:
1738:
1733:
1728:
1726:Wurtz reaction
1723:
1718:
1713:
1708:
1703:
1698:
1693:
1688:
1683:
1678:
1673:
1668:
1663:
1658:
1653:
1648:
1643:
1638:
1633:
1628:
1623:
1618:
1613:
1608:
1603:
1598:
1596:Prins reaction
1593:
1588:
1583:
1578:
1573:
1568:
1563:
1558:
1553:
1548:
1543:
1538:
1533:
1528:
1523:
1518:
1513:
1508:
1503:
1498:
1493:
1488:
1483:
1478:
1473:
1468:
1463:
1458:
1453:
1448:
1443:
1438:
1433:
1428:
1423:
1418:
1413:
1411:Hydrocyanation
1408:
1403:
1398:
1393:
1388:
1383:
1381:Henry reaction
1378:
1373:
1368:
1363:
1358:
1353:
1348:
1343:
1338:
1333:
1328:
1323:
1318:
1313:
1308:
1303:
1298:
1293:
1288:
1283:
1278:
1273:
1268:
1263:
1258:
1253:
1248:
1243:
1238:
1233:
1228:
1223:
1218:
1213:
1208:
1203:
1198:
1193:
1188:
1183:
1178:
1173:
1168:
1163:
1158:
1153:
1148:
1143:
1138:
1133:
1128:
1123:
1118:
1113:
1108:
1103:
1098:
1093:
1088:
1083:
1081:Aldol reaction
1078:
1073:
1068:
1062:
1060:
1055:Carbon-carbon
1052:
1051:
1040:
1039:
1034:
1032:Zaitsev's rule
1029:
1024:
1019:
1014:
1009:
1004:
999:
994:
989:
984:
979:
977:Steric effects
974:
969:
964:
959:
954:
949:
944:
939:
934:
929:
924:
919:
914:
909:
904:
899:
894:
889:
884:
879:
874:
869:
864:
859:
854:
849:
844:
839:
834:
829:
824:
819:
814:
809:
804:
799:
794:
789:
784:
779:
774:
769:
764:
759:
754:
749:
744:
739:
734:
729:
724:
719:
714:
709:
704:
699:
694:
689:
684:
679:
674:
669:
664:
658:
655:
654:
652:
651:
646:
641:
636:
631:
629:Redox reaction
626:
621:
616:
614:Polymerization
611:
606:
600:
597:
596:
588:
587:
580:
573:
565:
557:
556:
535:(4): 273–284.
515:
472:
446:
419:
396:
384:
372:
345:
336:
327:
322:
314:
304:
303:
301:
298:
297:
296:
291:
286:
281:
274:
271:
228:
225:
224:
223:
203:
202:
176:
175:
160:
159:
131:
128:
119:
116:Stereomutation
41:stereospecific
15:
9:
6:
4:
3:
2:
3892:
3881:
3878:
3877:
3875:
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:
3787:
3784:
3782:
3779:
3777:
3774:
3772:
3771:Herz reaction
3769:
3767:
3764:
3762:
3759:
3757:
3754:
3752:
3749:
3747:
3744:
3742:
3739:
3737:
3734:
3732:
3729:
3727:
3724:
3722:
3719:
3717:
3714:
3712:
3709:
3707:
3704:
3702:
3699:
3697:
3694:
3692:
3689:
3687:
3684:
3682:
3679:
3677:
3674:
3672:
3669:
3667:
3664:
3662:
3659:
3657:
3654:
3652:
3649:
3648:
3646:
3642:
3636:
3633:
3631:
3628:
3626:
3623:
3621:
3618:
3616:
3613:
3611:
3608:
3606:
3603:
3601:
3598:
3596:
3593:
3591:
3588:
3586:
3583:
3581:
3578:
3576:
3573:
3571:
3568:
3566:
3563:
3561:
3558:
3556:
3553:
3551:
3548:
3546:
3543:
3541:
3538:
3536:
3533:
3531:
3528:
3526:
3523:
3521:
3518:
3516:
3513:
3511:
3508:
3506:
3503:
3501:
3498:
3496:
3493:
3491:
3488:
3486:
3483:
3481:
3478:
3477:
3475:
3473:
3472:Cycloaddition
3469:
3463:
3460:
3458:
3455:
3453:
3450:
3448:
3445:
3443:
3440:
3438:
3435:
3433:
3430:
3428:
3425:
3423:
3420:
3418:
3415:
3413:
3410:
3408:
3405:
3403:
3400:
3398:
3395:
3393:
3390:
3388:
3385:
3383:
3380:
3378:
3375:
3373:
3370:
3368:
3365:
3363:
3360:
3358:
3355:
3353:
3350:
3348:
3345:
3343:
3340:
3338:
3335:
3333:
3330:
3328:
3325:
3323:
3320:
3318:
3317:Isay reaction
3315:
3313:
3310:
3308:
3305:
3303:
3300:
3298:
3295:
3293:
3290:
3288:
3285:
3283:
3280:
3278:
3275:
3273:
3270:
3268:
3265:
3263:
3260:
3258:
3255:
3253:
3250:
3248:
3245:
3243:
3240:
3238:
3235:
3233:
3230:
3228:
3225:
3223:
3220:
3218:
3215:
3213:
3212:Cycloaddition
3210:
3208:
3205:
3203:
3200:
3198:
3195:
3193:
3190:
3188:
3185:
3183:
3180:
3178:
3175:
3173:
3170:
3168:
3165:
3163:
3160:
3158:
3155:
3153:
3150:
3148:
3145:
3143:
3140:
3138:
3135:
3133:
3130:
3128:
3125:
3123:
3120:
3118:
3115:
3114:
3112:
3110:
3107:Ring forming
3104:
3098:
3095:
3093:
3090:
3088:
3085:
3083:
3080:
3078:
3075:
3073:
3070:
3068:
3065:
3063:
3060:
3058:
3055:
3053:
3050:
3048:
3045:
3043:
3040:
3038:
3035:
3033:
3030:
3028:
3025:
3023:
3020:
3018:
3015:
3013:
3010:
3008:
3007:Rupe reaction
3005:
3003:
3000:
2998:
2995:
2993:
2990:
2988:
2985:
2983:
2980:
2978:
2975:
2973:
2970:
2968:
2965:
2963:
2960:
2958:
2955:
2953:
2950:
2948:
2945:
2943:
2940:
2938:
2935:
2933:
2930:
2928:
2925:
2923:
2920:
2918:
2915:
2913:
2910:
2908:
2905:
2903:
2900:
2898:
2895:
2893:
2890:
2888:
2885:
2883:
2880:
2878:
2875:
2873:
2870:
2868:
2865:
2863:
2860:
2858:
2855:
2853:
2850:
2848:
2845:
2843:
2840:
2838:
2835:
2833:
2830:
2828:
2825:
2823:
2820:
2818:
2815:
2813:
2810:
2808:
2805:
2803:
2800:
2798:
2795:
2793:
2790:
2788:
2785:
2783:
2780:
2778:
2775:
2773:
2770:
2768:
2765:
2763:
2760:
2758:
2755:
2753:
2750:
2748:
2745:
2743:
2740:
2738:
2735:
2733:
2730:
2728:
2725:
2723:
2720:
2718:
2715:
2713:
2710:
2708:
2705:
2703:
2700:
2698:
2695:
2693:
2690:
2688:
2685:
2683:
2680:
2678:
2675:
2673:
2670:
2668:
2665:
2663:
2660:
2658:
2655:
2653:
2650:
2648:
2645:
2643:
2640:
2638:
2635:
2633:
2630:
2629:
2627:
2625:
2619:
2613:
2610:
2608:
2605:
2603:
2600:
2598:
2595:
2593:
2590:
2588:
2585:
2583:
2580:
2578:
2575:
2573:
2570:
2568:
2565:
2563:
2560:
2558:
2555:
2553:
2550:
2548:
2545:
2543:
2540:
2538:
2535:
2533:
2530:
2528:
2525:
2523:
2520:
2518:
2515:
2513:
2510:
2508:
2505:
2503:
2500:
2498:
2495:
2493:
2490:
2488:
2485:
2483:
2480:
2478:
2475:
2473:
2470:
2468:
2465:
2463:
2460:
2458:
2455:
2453:
2450:
2448:
2445:
2443:
2440:
2438:
2435:
2433:
2430:
2428:
2425:
2423:
2420:
2418:
2415:
2413:
2410:
2408:
2405:
2403:
2400:
2398:
2397:Ley oxidation
2395:
2393:
2390:
2388:
2385:
2383:
2380:
2378:
2375:
2373:
2370:
2368:
2365:
2363:
2362:Hydroxylation
2360:
2358:
2355:
2353:
2352:Hydrogenation
2350:
2348:
2345:
2343:
2340:
2338:
2335:
2333:
2330:
2328:
2325:
2323:
2320:
2318:
2315:
2313:
2310:
2308:
2305:
2303:
2300:
2298:
2295:
2293:
2290:
2288:
2287:DNA oxidation
2285:
2283:
2280:
2278:
2277:Deoxygenation
2275:
2273:
2270:
2268:
2265:
2263:
2260:
2258:
2255:
2253:
2250:
2248:
2245:
2243:
2240:
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:
2167:Aromatization
2165:
2163:
2160:
2158:
2155:
2153:
2150:
2148:
2145:
2143:
2140:
2138:
2135:
2133:
2130:
2128:
2125:
2124:
2122:
2120:
2114:
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:
2039:
2037:
2031:
2025:
2022:
2020:
2017:
2015:
2012:
2010:
2007:
2005:
2004:Reed reaction
2002:
2000:
1997:
1995:
1992:
1990:
1987:
1985:
1982:
1980:
1977:
1975:
1972:
1970:
1967:
1965:
1962:
1960:
1957:
1955:
1952:
1950:
1947:
1945:
1942:
1940:
1937:
1935:
1932:
1930:
1927:
1925:
1922:
1921:
1919:
1915:bond forming
1911:
1901:
1898:
1896:
1893:
1891:
1888:
1886:
1883:
1881:
1878:
1876:
1873:
1871:
1868:
1866:
1863:
1861:
1858:
1856:
1853:
1851:
1848:
1846:
1843:
1841:
1838:
1836:
1833:
1831:
1828:
1826:
1823:
1821:
1820:Cope reaction
1818:
1816:
1813:
1811:
1808:
1806:
1803:
1801:
1798:
1797:
1795:
1791:
1785:
1782:
1780:
1777:
1775:
1772:
1770:
1767:
1765:
1762:
1760:
1757:
1755:
1752:
1751:
1749:
1747:
1743:
1737:
1734:
1732:
1729:
1727:
1724:
1722:
1719:
1717:
1714:
1712:
1709:
1707:
1704:
1702:
1699:
1697:
1694:
1692:
1689:
1687:
1684:
1682:
1679:
1677:
1674:
1672:
1669:
1667:
1664:
1662:
1659:
1657:
1654:
1652:
1649:
1647:
1644:
1642:
1639:
1637:
1634:
1632:
1629:
1627:
1624:
1622:
1619:
1617:
1614:
1612:
1609:
1607:
1604:
1602:
1599:
1597:
1594:
1592:
1589:
1587:
1584:
1582:
1579:
1577:
1574:
1572:
1569:
1567:
1564:
1562:
1559:
1557:
1554:
1552:
1549:
1547:
1544:
1542:
1539:
1537:
1534:
1532:
1531:Nef synthesis
1529:
1527:
1524:
1522:
1519:
1517:
1514:
1512:
1509:
1507:
1506:Methylenation
1504:
1502:
1499:
1497:
1494:
1492:
1489:
1487:
1484:
1482:
1479:
1477:
1474:
1472:
1469:
1467:
1464:
1462:
1459:
1457:
1454:
1452:
1449:
1447:
1444:
1442:
1439:
1437:
1434:
1432:
1429:
1427:
1424:
1422:
1419:
1417:
1414:
1412:
1409:
1407:
1404:
1402:
1399:
1397:
1394:
1392:
1389:
1387:
1384:
1382:
1379:
1377:
1376:Heck reaction
1374:
1372:
1369:
1367:
1364:
1362:
1359:
1357:
1354:
1352:
1349:
1347:
1344:
1342:
1339:
1337:
1334:
1332:
1329:
1327:
1324:
1322:
1319:
1317:
1314:
1312:
1309:
1307:
1304:
1302:
1299:
1297:
1294:
1292:
1289:
1287:
1284:
1282:
1279:
1277:
1274:
1272:
1269:
1267:
1264:
1262:
1259:
1257:
1254:
1252:
1249:
1247:
1244:
1242:
1239:
1237:
1234:
1232:
1229:
1227:
1224:
1222:
1219:
1217:
1214:
1212:
1209:
1207:
1204:
1202:
1199:
1197:
1194:
1192:
1189:
1187:
1184:
1182:
1179:
1177:
1174:
1172:
1169:
1167:
1164:
1162:
1159:
1157:
1154:
1152:
1149:
1147:
1144:
1142:
1139:
1137:
1134:
1132:
1129:
1127:
1124:
1122:
1119:
1117:
1114:
1112:
1109:
1107:
1104:
1102:
1099:
1097:
1094:
1092:
1089:
1087:
1084:
1082:
1079:
1077:
1074:
1072:
1069:
1067:
1064:
1063:
1061:
1057:bond forming
1053:
1049:
1044:
1038:
1035:
1033:
1030:
1028:
1025:
1023:
1022:Y-aromaticity
1020:
1018:
1015:
1013:
1010:
1008:
1007:Walsh diagram
1005:
1003:
1000:
998:
995:
993:
992:Taft equation
990:
988:
985:
983:
980:
978:
975:
973:
970:
968:
965:
963:
962:Σ-aromaticity
960:
958:
955:
953:
950:
948:
945:
943:
940:
938:
935:
933:
930:
928:
925:
923:
920:
918:
915:
913:
910:
908:
905:
903:
900:
898:
895:
893:
890:
888:
887:Marcus theory
885:
883:
880:
878:
875:
873:
870:
868:
865:
863:
862:Hückel's rule
860:
858:
855:
853:
850:
848:
845:
843:
840:
838:
835:
833:
830:
828:
825:
823:
820:
818:
817:Evelyn effect
815:
813:
810:
808:
805:
803:
800:
798:
797:Electron-rich
795:
793:
790:
788:
785:
783:
780:
778:
775:
773:
770:
768:
765:
763:
760:
758:
755:
753:
750:
748:
745:
743:
740:
738:
735:
733:
730:
728:
725:
723:
720:
718:
715:
713:
712:Bema Hapothle
710:
708:
705:
703:
700:
698:
695:
693:
690:
688:
685:
683:
680:
678:
675:
673:
670:
668:
665:
663:
660:
659:
656:
650:
647:
645:
642:
640:
637:
635:
632:
630:
627:
625:
622:
620:
617:
615:
612:
610:
607:
605:
602:
601:
598:
594:
586:
581:
579:
574:
572:
567:
566:
563:
552:
548:
543:
538:
534:
530:
526:
519:
511:
507:
503:
499:
495:
491:
487:
483:
476:
470:
466:
462:
459:
455:
450:
444:
440:
436:
432:
428:
423:
417:
413:
409:
405:
400:
394:
388:
382:
376:
370:
366:
362:
358:
354:
349:
340:
331:
318:
309:
305:
295:
292:
290:
287:
285:
282:
280:
277:
276:
270:
268:
263:
261:
260:
255:
251:
247:
243:
242:
237:
233:
221:
217:
216:
215:
213:
208:
200:
196:
195:
194:
192:
188:
185:
181:
173:
169:
168:
167:
164:
157:
153:
152:
151:
149:
145:
141:
137:
127:
125:
117:
113:
110:
108:
104:
102:
97:
93:
88:
86:
82:
78:
74:
70:
65:
62:
58:
54:
50:
46:
42:
39:during a non-
38:
37:stereoisomers
34:
30:
26:
22:
2812:Ene reaction
2172:Autoxidation
2033:Degradation
1924:Azo coupling
1701:Ugi reaction
1301:Ene reaction
1101:Alkynylation
952:Polyfluorene
947:Polar effect
812:Electrophile
727:Bredt's rule
697:Baird's rule
667:Alpha effect
638:
532:
528:
518:
485:
481:
475:
460:
453:
449:
434:
426:
422:
410:: 3428-3436
407:
403:
399:
387:
375:
360:
352:
348:
339:
330:
317:
308:
264:
257:
239:
230:
204:
177:
161:
143:
139:
133:
115:
114:
111:
106:
105:
96:diastereomer
91:
89:
68:
66:
45:stereocenter
24:
18:
1311:Ethenolysis
957:Ring strain
927:Nucleophile
752:Clar's rule
692:Aromaticity
246:pinoresinol
232:Pinoresinol
207:stereogenic
163:Cram's rule
3595:Ozonolysis
3122:Annulation
2472:Ozonolysis
591:Topics in
73:enantiomer
3109:reactions
2624:reactions
2119:reactions
2035:reactions
1917:reactions
1059:reactions
551:195313754
21:chemistry
3874:Category
1002:Vinylogy
672:Annulene
619:Reagents
510:41957412
273:See also
130:Examples
33:reactant
662:A value
502:8994027
482:Science
212:t-butyl
205:With a
184:achiral
55:in the
549:
508:
500:
77:enzyme
49:steric
547:S2CID
506:S2CID
463:, 48
248:from
140:trans
498:PMID
461:2009
435:2005
408:2005
393:Link
381:Link
361:1973
178:The
51:and
537:doi
490:doi
486:275
465:doi
439:doi
412:doi
365:doi
144:cis
67:An
19:In
3876::
545:.
533:53
531:.
527:.
504:.
496:.
484:.
433:,
359:;
103:.
90:A
23:,
584:e
577:t
570:v
553:.
539::
512:.
492::
467::
441::
414::
367::
323:N
120:N
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
