158:
329:
238:
165:
387:
364:
811:
Wrobleski, Aaron; Sahasrabudhe, Kiran; Aubé, Jeffrey (May 2004). "Asymmetric Total
Synthesis of Dendrobatid Alkaloids: Preparation of Indolizidine 251F and Its 3-Desmethyl Analogue Using an Intramolecular Schmidt Reaction Strategy".
188:). (In the Curtius rearrangement, sodium azide and an acyl chloride are combined to quantitatively generate the acyl azide intermediate, and the rest of the reaction takes place under neutral conditions.)
668:
Crosby, Ian T.; Shin, James K.; Capuano, Ben (2010). "The
Application of the Schmidt Reaction and Beckmann Rearrangement to the Synthesis of Bicyclic Lactams: Some Mechanistic Considerations".
1803:
328:
237:
731:
Milligan, Gregory L.; Mossman, Craig J.; Aube, Jeffrey (October 1995). "Intramolecular
Schmidt Reactions of Alkyl Azides with Ketones: Scope and Stereochemical Studies".
180:
except that in this reaction the acyl azide is produced by reaction of the carboxylic acid with hydrazoic acid via the protonated carboxylic acid, in a process akin to a
4018:
127:
3134:
3079:
3847:
3189:
184:. An alternative, involving the formation of an acylium ion, becomes more important when the reaction takes place in concentrated acid (>90%
3339:
1973:
4068:
261:
to diazoiminium 5. One of the alkyl or aryl groups migrates from carbon to nitrogen with loss of nitrogen to give a nitrilium intermediate
69:
3842:
1668:
2944:
865:
3514:
2714:
1458:
3679:
3609:
3589:
3084:
2251:
1713:
2132:
1688:
901:
3434:
325:, the group that migrates can sometimes change, depending on the conditions used, to deliver either of the two possible amides.
3912:
3862:
2266:
3369:
4008:
3817:
3474:
3454:
3414:
2221:
1164:
617:
Koldobskii, G I; Ostrovskii, Vladimir A; Gidaspov, B V (1978-11-30). "Schmidt
Reaction with Aldehydes and Carboxylic Acids".
321:(the Baeyer-Villiger pathway). These possibilities have been used to account for the fact that, for certain substrates like
4003:
3933:
3832:
3489:
3344:
2974:
2819:
2429:
2056:
1833:
146:
was not reported until 1991 but has become important in the synthesis of natural products. The reaction is effective with
4083:
3867:
3179:
2669:
2344:
2889:
4172:
4078:
3792:
3654:
3444:
3409:
472:
3968:
3907:
3439:
3354:
3324:
3304:
3169:
3164:
2539:
2464:
2107:
2061:
1928:
1189:
439:
181:
4162:
4073:
4033:
3983:
3659:
3459:
3209:
3139:
1628:
1199:
3274:
2167:
1888:
3827:
3669:
3539:
3534:
3349:
2824:
2734:
2324:
2256:
2147:
1723:
1478:
1403:
858:
3584:
4113:
3998:
3897:
3837:
3484:
3279:
3239:
3214:
3124:
2584:
1618:
1548:
1184:
1114:
2704:
4103:
3689:
3579:
3199:
2924:
2709:
2654:
2499:
2459:
2291:
2046:
1763:
1613:
760:"Cation–π Control of Regiochemistry of Intramolecular Schmidt Reactions en Route to Bridged Bicyclic Lactams"
294:
4063:
3624:
3069:
4098:
4013:
3988:
3963:
3948:
3872:
3787:
3684:
3644:
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3464:
3229:
2774:
2759:
2624:
2414:
2082:
1838:
1518:
1493:
1463:
1054:
703:
J. H. Boyer & J. Hamer (1955). "The Acid-catalyzed
Reaction of Alkyl Azides upon Carbonyl Compounds".
4048:
3993:
3938:
3649:
3569:
3469:
3184:
3149:
2994:
2884:
2599:
2594:
2419:
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2051:
1903:
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1748:
1608:
1468:
1418:
1413:
1388:
1348:
1294:
1059:
1049:
1024:
54:
4023:
3724:
3529:
2964:
2849:
2529:
2504:
2444:
2301:
2036:
1743:
1523:
1488:
1393:
1084:
1019:
851:
62:
3314:
1578:
4123:
4028:
3882:
3762:
3734:
3704:
3619:
3549:
3504:
3479:
3399:
3299:
3259:
2954:
2574:
2564:
2489:
2013:
1873:
1868:
1848:
1533:
1330:
1309:
1269:
1194:
157:
1014:
4088:
3978:
3958:
3822:
3664:
3574:
3544:
3524:
3419:
3374:
3204:
3114:
3044:
2929:
2919:
2749:
2306:
2246:
2211:
2018:
1998:
1958:
1733:
1603:
1568:
1528:
1279:
1119:
1109:
1039:
3554:
553:
Jeffrey Aube & Gregory L. Milligan (1991). "Intramolecular
Schmidt reaction of alkyl azides".
4167:
4058:
3917:
3767:
3709:
3634:
3614:
3334:
3284:
3144:
3109:
3049:
2979:
2534:
2281:
2261:
1993:
1913:
1808:
1768:
1738:
1673:
1558:
1543:
1453:
1443:
1104:
1029:
984:
143:
1319:
3797:
3519:
3269:
3249:
3224:
3174:
3089:
3064:
3019:
2989:
2969:
2939:
2904:
2859:
2834:
2809:
2694:
2619:
2399:
2092:
2028:
1828:
1553:
1473:
1159:
1134:
911:
906:
266:
215:
with the alkyl group R, migrating over the C-N bond with expulsion of nitrogen. The protonated
212:
38:
4133:
3719:
3674:
3389:
3359:
3329:
3264:
3244:
3159:
3154:
3119:
3074:
3059:
3054:
3034:
3024:
2959:
2949:
2879:
2829:
2349:
2152:
1728:
1683:
1513:
1503:
1249:
1174:
969:
931:
405:
400:
250:
177:
1179:
371:
Variations involving intramolecular
Schmidt reactions have been known since 1991. These are
301:. Loss of a proton again furnishes the amide. It has been proposed that the dehydration to
3902:
3852:
3802:
3782:
3772:
3629:
3604:
3319:
3309:
3194:
3009:
3004:
2934:
2719:
2519:
2479:
2409:
2374:
2329:
2296:
2162:
2137:
2117:
1938:
1898:
1858:
1823:
1753:
1508:
1378:
1353:
891:
626:
410:
332:
Two proposed reaction mechanisms for the amide formation from a ketone via
Schmidt reaction
258:
164:
8:
4108:
4093:
3739:
3714:
3699:
3694:
3424:
3379:
3364:
3254:
3234:
3129:
3014:
2999:
2844:
2789:
2779:
2744:
2509:
2384:
2359:
2271:
2127:
2112:
2097:
1918:
1863:
1633:
1483:
1428:
1299:
1214:
1074:
999:
357:
4118:
2769:
1953:
1144:
630:
3857:
3807:
3777:
3639:
3429:
3219:
3104:
3039:
3029:
2794:
2724:
2689:
2684:
2664:
2659:
2604:
2514:
2364:
2226:
2216:
2122:
1908:
1853:
1783:
1703:
1598:
1498:
1433:
1358:
1204:
1069:
1004:
989:
788:
759:
650:
241:
Reaction mechanism for the amine formation from a carboxylic acid via
Schmidt reaction.
488:
Lang, S.; Murphy, J. A. (2006). "Azide rearrangements in electron-deficient systems".
3594:
2914:
2799:
2764:
2729:
2674:
2629:
2544:
2524:
2474:
2469:
2439:
2424:
2334:
2241:
2177:
2142:
1968:
1843:
1718:
1643:
1623:
1538:
1373:
1368:
1314:
1224:
1129:
1089:
1044:
926:
921:
886:
829:
793:
767:
705:
685:
654:
642:
555:
505:
468:
435:
83:
2589:
638:
4128:
3973:
3943:
3887:
3812:
3744:
3499:
3449:
3099:
2874:
2869:
2814:
2804:
2579:
2389:
2369:
2339:
2236:
2172:
2157:
1988:
1943:
1933:
1923:
1818:
1798:
1793:
1778:
1773:
1653:
1648:
1588:
1573:
1563:
1408:
1398:
1264:
1254:
1154:
1149:
1124:
1064:
916:
875:
821:
783:
775:
740:
713:
677:
634:
597:
563:
532:
497:
460:
91:
1244:
344:
The scope of this reaction has been extended to reactions of carbonyls with alkyl
4038:
3729:
3564:
3559:
2854:
2839:
2784:
2739:
2699:
2649:
2614:
2609:
2554:
2549:
2484:
2434:
2354:
2182:
2066:
2041:
2003:
1978:
1963:
1948:
1883:
1758:
1708:
1698:
1678:
1638:
1448:
1438:
1423:
1219:
1139:
1009:
979:
964:
959:
147:
111:
464:
4043:
3953:
3892:
2984:
2894:
2864:
2639:
2494:
2231:
2008:
1878:
1693:
1663:
1363:
1259:
1034:
896:
602:
585:
227:
204:
135:
843:
375:
reactions and have some utility in the synthesis of natural products; such as
309:(and, hence, the Beckmann pathway) is favored by nonaqueous acids like conc. H
4156:
4053:
3754:
3599:
3494:
3289:
2679:
2644:
2634:
2569:
2559:
2449:
2286:
2102:
1813:
1788:
1658:
1304:
1289:
1274:
1169:
1099:
1079:
994:
689:
646:
536:
386:
185:
586:"Intramolecular Schmidt Reaction: Applications in Natural Product Synthesis"
3094:
2454:
2206:
1983:
1583:
1383:
1234:
1229:
1094:
949:
833:
797:
509:
352:. This extension was first reported by J.H. Boyer in 1955 (hence the name
131:
1593:
1239:
1209:
974:
322:
200:
139:
744:
717:
567:
3877:
3404:
2754:
372:
216:
825:
779:
130:(1887–1971), who first reported it in 1924 by successfully converting
501:
380:
220:
681:
1284:
954:
278:
123:
103:
99:
944:
192:
363:
552:
525:
Berichte der
Deutschen Chemischen Gesellschaft (A and B Series)
429:
376:
345:
246:
151:
107:
277:, which undergoes loss of proton to arrive at the imidic acid
282:
231:
119:
115:
95:
616:
16:
Chemical reaction between an azide and a carbonyl derivative
317:, while aqueous acids like conc. HCl favor migration from
810:
285:. In an alternative mechanism, the migration occurs at
245:
In the reaction mechanism for the Schmidt reaction of
249:, the carbonyl group is activated by protonation for
4019:
Erlenmeyer–Plöchl azlactone and amino-acid synthesis
757:
730:
702:
434:(2nd ed.). Chichester: John Wiley & Sons.
339:
3080:Divinylcyclopropane-cycloheptadiene rearrangement
667:
191:The carboxylic acid Schmidt reaction starts with
4154:
584:Nyfeler, Erich; Renaud, Philippe (24 May 2006).
873:
3340:Thermal rearrangement of aromatic hydrocarbons
1974:Thermal rearrangement of aromatic hydrocarbons
579:
577:
4069:Lectka enantioselective beta-lactam synthesis
1329:
859:
583:
523:Schmidt, K. F. (1924). "Ăśber den Imin-Rest".
289:, directly after protonation of intermediate
3848:Inverse electron-demand Diels–Alder reaction
1669:Heterogeneous metal catalyzed cross-coupling
455:Wolff, Hans (2011). "The Schmidt Reaction".
3190:Lobry de Bruyn–Van Ekenstein transformation
574:
866:
852:
590:CHIMIA International Journal for Chemistry
487:
430:Plagens, Andreas; Laue, Thomas M. (2005).
3680:Petrenko-Kritschenko piperidone synthesis
3135:Fritsch–Buttenberg–Wiechell rearrangement
787:
601:
3843:Intramolecular Diels–Alder cycloaddition
814:Journal of the American Chemical Society
733:Journal of the American Chemical Society
448:
385:
362:
548:
546:
522:
176:The reaction is closely related to the
4155:
3863:Metal-centered cycloaddition reactions
3515:Debus–Radziszewski imidazole synthesis
1459:Bodroux–Chichibabin aldehyde synthesis
4009:Diazoalkane 1,3-dipolar cycloaddition
3913:Vinylcyclopropane (5+2) cycloaddition
3818:Diazoalkane 1,3-dipolar cycloaddition
3590:Hurd–Mori 1,2,3-thiadiazole synthesis
3085:Dowd–Beckwith ring-expansion reaction
2252:Hurd–Mori 1,2,3-thiadiazole synthesis
1328:
1165:LFER solvent coefficients (data page)
847:
454:
171:
114:, under acidic conditions to give an
2820:Sharpless asymmetric dihydroxylation
2057:Methoxymethylenetriphenylphosphorane
543:
2945:Allen–Millar–Trippett rearrangement
758:Lei Yao & Jeffrey Aubé (2007).
13:
4084:Nitrone-olefin (3+2) cycloaddition
4079:Niementowski quinazoline synthesis
3868:Nitrone-olefin (3+2) cycloaddition
3793:Azide-alkyne Huisgen cycloaddition
3655:Niementowski quinazoline synthesis
3410:Azide-alkyne Huisgen cycloaddition
2715:Meerwein–Ponndorf–Verley reduction
2267:Leimgruber–Batcho indole synthesis
327:
253:by the azide, forming azidohydrin
236:
226:, which after deprotonation loses
207:forms the protonated azido ketone
163:
156:
14:
4184:
3908:Trimethylenemethane cycloaddition
3610:Johnson–Corey–Chaykovsky reaction
3475:Cadogan–Sundberg indole synthesis
3455:Bohlmann–Rahtz pyridine synthesis
3415:Baeyer–Emmerling indole synthesis
2222:Cadogan–Sundberg indole synthesis
1714:Johnson–Corey–Chaykovsky reaction
203:and loss of water. Reaction with
150:to give amines (above), and with
4004:Cook–Heilbron thiazole synthesis
3833:Hexadehydro Diels–Alder reaction
3660:Niementowski quinoline synthesis
3490:Cook–Heilbron thiazole synthesis
3435:Bischler–Möhlau indole synthesis
3345:Tiffeneau–Demjanov rearrangement
2975:Baker–Venkataraman rearrangement
2133:Horner–Wadsworth–Emmons reaction
1804:Mizoroki-Heck vs. Reductive Heck
1689:Horner–Wadsworth–Emmons reaction
1200:Neighbouring group participation
356:), for example, the reaction of
340:Reactions involving alkyl azides
3540:Fiesselmann thiophene synthesis
3370:Westphalen–Lettré rearrangement
3350:Vinylcyclopropane rearrangement
3180:Kornblum–DeLaMare rearrangement
2825:Epoxidation of allylic alcohols
2735:Noyori asymmetric hydrogenation
2670:Kornblum–DeLaMare rearrangement
2345:Gallagher–Hollander degradation
804:
751:
724:
670:Australian Journal of Chemistry
639:10.1070/rc1978v047n11abeh002294
390:Intramolecular Schmidt reaction
3999:Chichibabin pyridine synthesis
3485:Chichibabin pyridine synthesis
3445:Blum–Ittah aziridine synthesis
3280:Ring expansion and contraction
1549:Cross dehydrogenative coupling
696:
661:
610:
516:
481:
423:
1:
3969:Bischler–Napieralski reaction
3927:Heterocycle forming reactions
3580:Hemetsberger indole synthesis
3440:Bischler–Napieralski reaction
3355:Wagner–Meerwein rearrangement
3325:Sommelet–Hauser rearrangement
3305:Seyferth–Gilbert homologation
3170:Ireland–Claisen rearrangement
3165:Hofmann–Martius rearrangement
2925:2,3-sigmatropic rearrangement
2540:Corey–Winter olefin synthesis
2465:Barton–McCombie deoxygenation
2108:Corey–Winter olefin synthesis
2062:Seyferth–Gilbert homologation
1929:Seyferth–Gilbert homologation
416:
293:, in a manner similar to the
219:is attacked by water forming
4074:Lehmstedt–Tanasescu reaction
4034:Gabriel–Colman rearrangement
3989:Bucherer carbazole synthesis
3984:Borsche–Drechsel cyclization
3964:Bernthsen acridine synthesis
3949:Bamberger triazine synthesis
3934:Algar–Flynn–Oyamada reaction
3645:Nazarov cyclization reaction
3510:De Kimpe aziridine synthesis
3465:Bucherer carbazole synthesis
3460:Borsche–Drechsel cyclization
3230:Nazarov cyclization reaction
3210:Meyer–Schuster rearrangement
3140:Gabriel–Colman rearrangement
2890:Wolffenstein–Böters reaction
2775:Reduction of nitro compounds
2625:Grundmann aldehyde synthesis
2430:Algar–Flynn–Oyamada reaction
1839:Olefin conversion technology
1834:Nozaki–Hiyama–Kishi reaction
1629:Gabriel–Colman rearrangement
1519:Claisen-Schmidt condensation
1464:Bouveault aldehyde synthesis
7:
4049:Hantzsch pyridine synthesis
3828:Enone–alkene cycloadditions
3650:Nenitzescu indole synthesis
3570:Hantzsch pyridine synthesis
3535:Ferrario–Ackermann reaction
3185:Kowalski ester homologation
3150:Halogen dance rearrangement
2995:Benzilic acid rearrangement
2420:Akabori amino-acid reaction
2380:Von Braun amide degradation
2325:Barbier–Wieland degradation
2277:Nenitzescu indole synthesis
2257:Kharasch–Sosnovsky reaction
2148:Julia–Kocienski olefination
2052:Kowalski ester homologation
1749:Kowalski ester homologation
1724:Julia–Kocienski olefination
1479:Cadiot–Chodkiewicz coupling
1404:Aza-Baylis–Hillman reaction
1349:Acetoacetic ester synthesis
1060:Dynamic binding (chemistry)
1050:Conrotatory and disrotatory
1025:Charge remote fragmentation
465:10.1002/0471264180.or003.08
394:
269:. Attack by water converts
10:
4189:
4114:Robinson–Gabriel synthesis
4064:Kröhnke pyridine synthesis
3898:Retro-Diels–Alder reaction
3838:Imine Diels–Alder reaction
3625:Kröhnke pyridine synthesis
3240:Newman–Kwart rearrangement
3215:Mislow–Evans rearrangement
3125:Fischer–Hepp rearrangement
3070:Di-Ď€-methane rearrangement
2850:Stephen aldehyde synthesis
2585:Eschweiler–Clarke reaction
2302:Williamson ether synthesis
1619:Fujiwara–Moritani reaction
1524:Combes quinoline synthesis
1489:Carbonyl olefin metathesis
1190:More O'Ferrall–Jencks plot
1115:Grunwald–Winstein equation
1085:Electron-withdrawing group
1020:Catalytic resonance theory
603:10.2533/000942906777674714
273:to protonated imidic acid
257:, which loses water in an
4173:Amide synthesis reactions
4124:Urech hydantoin synthesis
4104:Pomeranz–Fritsch reaction
4029:Fischer oxazole synthesis
3926:
3763:1,3-Dipolar cycloaddition
3753:
3735:Urech hydantoin synthesis
3705:Reissert indole synthesis
3690:Pomeranz–Fritsch reaction
3620:Knorr quinoline synthesis
3550:Fischer oxazole synthesis
3480:Camps quinoline synthesis
3400:1,3-Dipolar cycloaddition
3388:
3300:Semipinacol rearrangement
3275:Ramberg–Bäcklund reaction
3260:Piancatelli rearrangement
3200:McFadyen–Stevens reaction
2955:Alpha-ketol rearrangement
2903:
2710:McFadyen–Stevens reaction
2655:Kiliani–Fischer synthesis
2575:Elbs persulfate oxidation
2500:Bouveault–Blanc reduction
2460:Baeyer–Villiger oxidation
2398:
2315:
2292:Schotten–Baumann reaction
2195:
2168:Ramberg–Bäcklund reaction
2075:
2047:Kiliani–Fischer synthesis
2027:
1889:Ramberg–Bäcklund reaction
1874:Pinacol coupling reaction
1869:Piancatelli rearrangement
1764:Liebeskind–Srogl coupling
1614:Fujimoto–Belleau reaction
1337:
1331:List of organic reactions
1195:Negative hyperconjugation
940:
882:
297:to give protonated amide
295:Baeyer–Villiger oxidation
76:
50:Organic Chemistry Portal
44:
21:
4099:Pictet–Spengler reaction
4014:Einhorn–Brunner reaction
3979:Boger pyridine synthesis
3873:Oxo-Diels–Alder reaction
3788:Aza-Diels–Alder reaction
3685:Pictet–Spengler reaction
3585:Hofmann–Löffler reaction
3575:Hegedus indole synthesis
3545:Fischer indole synthesis
3420:Bartoli indole synthesis
3375:Willgerodt rearrangement
3205:McLafferty rearrangement
3115:Ferrier carbocyclization
2930:2,3-Wittig rearrangement
2920:1,2-Wittig rearrangement
2760:Parikh–Doering oxidation
2750:Oxygen rebound mechanism
2415:Adkins–Peterson reaction
2307:Yamaguchi esterification
2247:Hegedus indole synthesis
2212:Bartoli indole synthesis
2083:Bamford–Stevens reaction
1999:Weinreb ketone synthesis
1959:Stork enamine alkylation
1734:Knoevenagel condensation
1604:Ferrier carbocyclization
1494:Castro–Stephens coupling
1120:Hammett acidity function
1110:Free-energy relationship
1055:Curtin–Hammett principle
1040:Conformational isomerism
619:Russian Chemical Reviews
537:10.1002/cber.19240570423
154:to give amides (below).
4163:Rearrangement reactions
4059:Knorr pyrrole synthesis
3994:Bucherer–Bergs reaction
3939:Allan–Robinson reaction
3918:Wagner-Jauregg reaction
3710:Ring-closing metathesis
3635:Larock indole synthesis
3615:Knorr pyrrole synthesis
3470:Bucherer–Bergs reaction
3335:Stieglitz rearrangement
3315:Skattebøl rearrangement
3285:Ring-closing metathesis
3145:Group transfer reaction
3110:Favorskii rearrangement
3050:Cornforth rearrangement
2980:Bamberger rearrangement
2885:Wolff–Kishner reduction
2705:Markó–Lam deoxygenation
2600:Fleming–Tamao oxidation
2595:Fischer–Tropsch process
2282:Oxymercuration reaction
2262:Knorr pyrrole synthesis
2088:Barton–Kellogg reaction
1994:Wagner-Jauregg reaction
1914:Ring-closing metathesis
1904:Reimer–Tiemann reaction
1894:Rauhut–Currier reaction
1809:Nef isocyanide reaction
1769:Malonic ester synthesis
1739:Knorr pyrrole synthesis
1674:High dilution principle
1609:Friedel–Crafts reaction
1544:Cross-coupling reaction
1469:Bucherer–Bergs reaction
1454:Blanc chloromethylation
1444:Blaise ketone synthesis
1419:Baylis–Hillman reaction
1414:Barton–Kellogg reaction
1389:Allan–Robinson reaction
1295:Woodward–Hoffmann rules
1030:Charge-transfer complex
432:Named organic reactions
211:, which goes through a
144:intramolecular reaction
102:derivative, usually an
30:Karl Friedrich Schmidt
4024:Feist–Benary synthesis
3798:Bradsher cycloaddition
3768:4+4 Photocycloaddition
3725:Simmons–Smith reaction
3670:Paternò–Büchi reaction
3530:Feist–Benary synthesis
3520:Dieckmann condensation
3270:Pummerer rearrangement
3250:Oxy-Cope rearrangement
3225:Myers allene synthesis
3175:Jacobsen rearrangement
3090:Electrocyclic reaction
3065:Demjanov rearrangement
3020:Buchner ring expansion
2990:Beckmann rearrangement
2970:Aza-Cope rearrangement
2965:Arndt–Eistert reaction
2940:Alkyne zipper reaction
2860:Transfer hydrogenation
2835:Sharpless oxyamination
2810:Selenoxide elimination
2695:Lombardo methylenation
2620:Griesbaum coozonolysis
2530:Corey–Itsuno reduction
2505:Boyland–Sims oxidation
2445:Angeli–Rimini reaction
2093:Boord olefin synthesis
2037:Arndt–Eistert reaction
2029:Homologation reactions
1829:Nitro-Mannich reaction
1744:Kolbe–Schmitt reaction
1554:Cross-coupling partner
1474:Buchner ring expansion
1394:Arndt–Eistert reaction
1160:Kinetic isotope effect
907:Rearrangement reaction
391:
368:
360:with β-azido ethanol:
333:
267:Beckmann rearrangement
242:
213:rearrangement reaction
182:Fischer esterification
168:
161:
128:Karl Friedrich Schmidt
39:Rearrangement reaction
3883:Pauson–Khand reaction
3720:Sharpless epoxidation
3675:Pechmann condensation
3555:Friedländer synthesis
3505:Davis–Beirut reaction
3360:Wallach rearrangement
3330:Stevens rearrangement
3265:Pinacol rearrangement
3245:Overman rearrangement
3160:Hofmann rearrangement
3155:Hayashi rearrangement
3120:Ferrier rearrangement
3075:Dimroth rearrangement
3060:Curtius rearrangement
3055:Criegee rearrangement
3035:Claisen rearrangement
3025:Carroll rearrangement
2960:Amadori rearrangement
2950:Allylic rearrangement
2830:Sharpless epoxidation
2565:Dess–Martin oxidation
2490:Bohn–Schmidt reaction
2350:Hofmann rearrangement
2153:Kauffmann olefination
2076:Olefination reactions
2014:Wurtz–Fittig reaction
1849:Palladium–NHC complex
1729:Kauffmann olefination
1684:Homologation reaction
1534:Corey–House synthesis
1514:Claisen rearrangement
1310:Yukawa–Tsuno equation
1270:Swain–Lupton equation
1250:Spherical aromaticity
1185:Möbius–Hückel concept
970:Aromatic ring current
932:Substitution reaction
406:Hofmann rearrangement
401:Curtius rearrangement
389:
366:
331:
251:nucleophilic addition
240:
178:Curtius rearrangement
167:
160:
4089:Paal–Knorr synthesis
3959:Barton–Zard reaction
3903:Staudinger synthesis
3853:Ketene cycloaddition
3823:Diels–Alder reaction
3803:Cheletropic reaction
3783:Alkyne trimerisation
3665:Paal–Knorr synthesis
3630:Kulinkovich reaction
3605:Jacobsen epoxidation
3525:Diels–Alder reaction
3320:Smiles rearrangement
3310:Sigmatropic reaction
3195:Lossen rearrangement
3045:Corey–Fuchs reaction
3010:Boekelheide reaction
3005:Bergmann degradation
2935:Achmatowicz reaction
2720:Methionine sulfoxide
2520:Clemmensen reduction
2480:Bergmann degradation
2410:Acyloin condensation
2375:Strecker degradation
2330:Bergmann degradation
2297:Ullmann condensation
2163:Peterson olefination
2138:Hydrazone iodination
2118:Elimination reaction
2019:Zincke–Suhl reaction
1939:Sonogashira coupling
1899:Reformatsky reaction
1859:Peterson olefination
1824:Nierenstein reaction
1754:Kulinkovich reaction
1569:Diels–Alder reaction
1529:Corey–Fuchs reaction
1509:Claisen condensation
1379:Alkyne trimerisation
1354:Acyloin condensation
1320:ÎŁ-bishomoaromaticity
1280:Thorpe–Ingold effect
892:Elimination reaction
411:Lossen rearrangement
259:elimination reaction
126:. It is named after
122:, with expulsion of
4109:Prilezhaev reaction
4094:Pellizzari reaction
3773:(4+3) cycloaddition
3740:Van Leusen reaction
3715:Robinson annulation
3700:Pschorr cyclization
3695:Prilezhaev reaction
3425:Bergman cyclization
3380:Wolff rearrangement
3365:Weerman degradation
3255:Pericyclic reaction
3235:Neber rearrangement
3130:Fries rearrangement
3015:Brook rearrangement
3000:Bergman cyclization
2845:Staudinger reaction
2790:Rosenmund reduction
2780:Reductive amination
2745:Oppenauer oxidation
2535:Corey–Kim oxidation
2510:Cannizzaro reaction
2385:Weerman degradation
2360:Isosaccharinic acid
2272:Mukaiyama hydration
2128:Hofmann elimination
2113:Dehydrohalogenation
2098:Chugaev elimination
1919:Robinson annulation
1864:Pfitzinger reaction
1634:Gattermann reaction
1579:Wulff–Dötz reaction
1559:Dakin–West reaction
1484:Carbonyl allylation
1429:Bergman cyclization
1215:Kennedy J. P. Orton
1135:Hammond's postulate
1105:Flippin–Lodge angle
1075:Electromeric effect
1000:Beta-silicon effect
985:Baker–Nathan effect
745:10.1021/ja00147a006
739:(42): 10449–10459.
718:10.1021/ja01609a045
631:1978RuCRv..47.1084K
568:10.1021/ja00023a065
358:3-nitrobenzaldehyde
3858:McCormack reaction
3808:Conia-ene reaction
3640:Madelung synthesis
3430:Biginelli reaction
3220:Mumm rearrangement
3105:Favorskii reaction
3040:Cope rearrangement
3030:Chan rearrangement
2795:Rubottom oxidation
2725:Miyaura borylation
2690:Lipid peroxidation
2685:Lindgren oxidation
2665:Kornblum oxidation
2660:Kolbe electrolysis
2605:Fukuyama reduction
2515:Carbonyl reduction
2365:Marker degradation
2227:Diazonium compound
2217:Boudouard reaction
2196:Carbon-heteroatom
2123:Grieco elimination
1909:Rieche formylation
1854:Passerini reaction
1784:Meerwein arylation
1704:Hydroxymethylation
1599:Favorskii reaction
1499:Chan rearrangement
1434:Biginelli reaction
1359:Aldol condensation
1205:2-Norbornyl cation
1180:Möbius aromaticity
1175:Markovnikov's rule
1070:Effective molarity
1015:Bürgi–Dunitz angle
1005:Bicycloaromaticity
392:
369:
367:The Boyer reaction
334:
243:
172:Reaction mechanism
169:
162:
4150:
4149:
4146:
4145:
4142:
4141:
4134:Wohl–Aue reaction
3778:6+4 Cycloaddition
3595:Iodolactonization
2915:1,2-rearrangement
2880:Wohl–Aue reaction
2800:Sabatier reaction
2765:Pinnick oxidation
2730:Mozingo reduction
2675:Leuckart reaction
2630:Haloform reaction
2545:Criegee oxidation
2525:Collins oxidation
2475:Benkeser reaction
2470:Bechamp reduction
2440:Andrussow process
2425:Alcohol oxidation
2335:Edman degradation
2242:Haloform reaction
2191:
2190:
2178:Takai olefination
2143:Julia olefination
1969:Takai olefination
1844:Olefin metathesis
1719:Julia olefination
1644:Grignard reaction
1624:Fukuyama coupling
1539:Coupling reaction
1504:Chan–Lam coupling
1374:Alkyne metathesis
1369:Alkane metathesis
1225:Phosphaethynolate
1130:George S. Hammond
1090:Electronic effect
1045:Conjugated system
927:Stereospecificity
922:Stereoselectivity
887:Addition reaction
876:organic reactions
826:10.1021/ja0320018
820:(17): 5475–5481.
780:10.1021/ja068919r
774:(10): 2766–2767.
768:J. Am. Chem. Soc.
706:J. Am. Chem. Soc.
625:(11): 1084–1094.
562:(23): 8965–8966.
556:J. Am. Chem. Soc.
457:Organic Reactions
84:organic chemistry
80:
79:
22:Schmidt reaction
4180:
4129:Wenker synthesis
4119:Stollé synthesis
3974:Bobbitt reaction
3944:Auwers synthesis
3888:Povarov reaction
3813:Cyclopropanation
3751:
3750:
3745:Wenker synthesis
3500:Darzens reaction
3450:Bobbitt reaction
3295:Schmidt reaction
3100:Enyne metathesis
2875:Whiting reaction
2870:Wharton reaction
2815:Shapiro reaction
2805:Sarett oxidation
2770:Prévost reaction
2580:Emde degradation
2390:Wohl degradation
2370:Ruff degradation
2340:Emde degradation
2237:Grignard reagent
2173:Shapiro reaction
2158:McMurry reaction
2025:
2024:
1989:Ullmann reaction
1954:Stollé synthesis
1944:Stetter reaction
1934:Shapiro reaction
1924:Sakurai reaction
1819:Negishi coupling
1799:Minisci reaction
1794:Michael reaction
1779:McMurry reaction
1774:Mannich reaction
1654:Hammick reaction
1649:Grignard reagent
1589:Enyne metathesis
1574:Doebner reaction
1564:Darzens reaction
1409:Barbier reaction
1399:Auwers synthesis
1326:
1325:
1300:Woodward's rules
1265:Superaromaticity
1255:Spiroaromaticity
1155:Inductive effect
1150:Hyperconjugation
1125:Hammett equation
1065:Edwards equation
917:Regioselectivity
868:
861:
854:
845:
844:
838:
837:
808:
802:
801:
791:
764:
755:
749:
748:
728:
722:
721:
700:
694:
693:
665:
659:
658:
614:
608:
607:
605:
581:
572:
571:
550:
541:
540:
520:
514:
513:
502:10.1039/B505080D
485:
479:
478:
452:
446:
445:
427:
148:carboxylic acids
92:organic reaction
88:Schmidt reaction
72:
57:
55:schmidt-reaction
19:
18:
4188:
4187:
4183:
4182:
4181:
4179:
4178:
4177:
4153:
4152:
4151:
4138:
4039:Gewald reaction
3922:
3749:
3730:Skraup reaction
3565:Graham reaction
3560:Gewald reaction
3391:
3384:
2906:
2899:
2855:Swern oxidation
2840:Stahl oxidation
2785:Riley oxidation
2740:Omega oxidation
2700:Luche reduction
2650:Jones oxidation
2615:Glycol cleavage
2610:Ganem oxidation
2555:Davis oxidation
2550:Dakin oxidation
2485:Birch reduction
2435:Amide reduction
2401:
2394:
2355:Hooker reaction
2317:
2311:
2199:
2197:
2187:
2183:Wittig reaction
2071:
2067:Wittig reaction
2042:Hooker reaction
2023:
2004:Wittig reaction
1979:Thorpe reaction
1964:Suzuki reaction
1949:Stille reaction
1884:Quelet reaction
1759:Kumada coupling
1709:Ivanov reaction
1699:Hydrovinylation
1679:Hiyama coupling
1639:Glaser coupling
1449:Blaise reaction
1439:Bingel reaction
1424:Benary reaction
1341:
1339:
1333:
1324:
1220:Passive binding
1140:Homoaromaticity
990:Baldwin's rules
965:Antiaromaticity
960:Anomeric effect
936:
878:
872:
842:
841:
809:
805:
763:(Communication)
762:
756:
752:
729:
725:
701:
697:
682:10.1071/CH09402
666:
662:
615:
611:
582:
575:
551:
544:
521:
517:
486:
482:
475:
453:
449:
442:
428:
424:
419:
397:
351:
342:
336:
316:
312:
174:
112:carboxylic acid
68:
53:
17:
12:
11:
5:
4186:
4176:
4175:
4170:
4168:Name reactions
4165:
4148:
4147:
4144:
4143:
4140:
4139:
4137:
4136:
4131:
4126:
4121:
4116:
4111:
4106:
4101:
4096:
4091:
4086:
4081:
4076:
4071:
4066:
4061:
4056:
4051:
4046:
4044:Hantzsch ester
4041:
4036:
4031:
4026:
4021:
4016:
4011:
4006:
4001:
3996:
3991:
3986:
3981:
3976:
3971:
3966:
3961:
3956:
3954:Banert cascade
3951:
3946:
3941:
3936:
3930:
3928:
3924:
3923:
3921:
3920:
3915:
3910:
3905:
3900:
3895:
3893:Prato reaction
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:
3759:
3757:
3748:
3747:
3742:
3737:
3732:
3727:
3722:
3717:
3712:
3707:
3702:
3697:
3692:
3687:
3682:
3677:
3672:
3667:
3662:
3657:
3652:
3647:
3642:
3637:
3632:
3627:
3622:
3617:
3612:
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:
3477:
3472:
3467:
3462:
3457:
3452:
3447:
3442:
3437:
3432:
3427:
3422:
3417:
3412:
3407:
3402:
3396:
3394:
3386:
3385:
3383:
3382:
3377:
3372:
3367:
3362:
3357:
3352:
3347:
3342:
3337:
3332:
3327:
3322:
3317:
3312:
3307:
3302:
3297:
3292:
3287:
3282:
3277:
3272:
3267:
3262:
3257:
3252:
3247:
3242:
3237:
3232:
3227:
3222:
3217:
3212:
3207:
3202:
3197:
3192:
3187:
3182:
3177:
3172:
3167:
3162:
3157:
3152:
3147:
3142:
3137:
3132:
3127:
3122:
3117:
3112:
3107:
3102:
3097:
3092:
3087:
3082:
3077:
3072:
3067:
3062:
3057:
3052:
3047:
3042:
3037:
3032:
3027:
3022:
3017:
3012:
3007:
3002:
2997:
2992:
2987:
2985:Banert cascade
2982:
2977:
2972:
2967:
2962:
2957:
2952:
2947:
2942:
2937:
2932:
2927:
2922:
2917:
2911:
2909:
2905:Rearrangement
2901:
2900:
2898:
2897:
2895:Zinin reaction
2892:
2887:
2882:
2877:
2872:
2867:
2865:Wacker process
2862:
2857:
2852:
2847:
2842:
2837:
2832:
2827:
2822:
2817:
2812:
2807:
2802:
2797:
2792:
2787:
2782:
2777:
2772:
2767:
2762:
2757:
2752:
2747:
2742:
2737:
2732:
2727:
2722:
2717:
2712:
2707:
2702:
2697:
2692:
2687:
2682:
2677:
2672:
2667:
2662:
2657:
2652:
2647:
2642:
2640:Hydrogenolysis
2637:
2632:
2627:
2622:
2617:
2612:
2607:
2602:
2597:
2592:
2590:Étard reaction
2587:
2582:
2577:
2572:
2567:
2562:
2557:
2552:
2547:
2542:
2537:
2532:
2527:
2522:
2517:
2512:
2507:
2502:
2497:
2495:Bosch reaction
2492:
2487:
2482:
2477:
2472:
2467:
2462:
2457:
2452:
2447:
2442:
2437:
2432:
2427:
2422:
2417:
2412:
2406:
2404:
2400:Organic redox
2396:
2395:
2393:
2392:
2387:
2382:
2377:
2372:
2367:
2362:
2357:
2352:
2347:
2342:
2337:
2332:
2327:
2321:
2319:
2313:
2312:
2310:
2309:
2304:
2299:
2294:
2289:
2284:
2279:
2274:
2269:
2264:
2259:
2254:
2249:
2244:
2239:
2234:
2232:Esterification
2229:
2224:
2219:
2214:
2209:
2203:
2201:
2193:
2192:
2189:
2188:
2186:
2185:
2180:
2175:
2170:
2165:
2160:
2155:
2150:
2145:
2140:
2135:
2130:
2125:
2120:
2115:
2110:
2105:
2100:
2095:
2090:
2085:
2079:
2077:
2073:
2072:
2070:
2069:
2064:
2059:
2054:
2049:
2044:
2039:
2033:
2031:
2022:
2021:
2016:
2011:
2009:Wurtz reaction
2006:
2001:
1996:
1991:
1986:
1981:
1976:
1971:
1966:
1961:
1956:
1951:
1946:
1941:
1936:
1931:
1926:
1921:
1916:
1911:
1906:
1901:
1896:
1891:
1886:
1881:
1879:Prins reaction
1876:
1871:
1866:
1861:
1856:
1851:
1846:
1841:
1836:
1831:
1826:
1821:
1816:
1811:
1806:
1801:
1796:
1791:
1786:
1781:
1776:
1771:
1766:
1761:
1756:
1751:
1746:
1741:
1736:
1731:
1726:
1721:
1716:
1711:
1706:
1701:
1696:
1694:Hydrocyanation
1691:
1686:
1681:
1676:
1671:
1666:
1664:Henry reaction
1661:
1656:
1651:
1646:
1641:
1636:
1631:
1626:
1621:
1616:
1611:
1606:
1601:
1596:
1591:
1586:
1581:
1576:
1571:
1566:
1561:
1556:
1551:
1546:
1541:
1536:
1531:
1526:
1521:
1516:
1511:
1506:
1501:
1496:
1491:
1486:
1481:
1476:
1471:
1466:
1461:
1456:
1451:
1446:
1441:
1436:
1431:
1426:
1421:
1416:
1411:
1406:
1401:
1396:
1391:
1386:
1381:
1376:
1371:
1366:
1364:Aldol reaction
1361:
1356:
1351:
1345:
1343:
1338:Carbon-carbon
1335:
1334:
1323:
1322:
1317:
1315:Zaitsev's rule
1312:
1307:
1302:
1297:
1292:
1287:
1282:
1277:
1272:
1267:
1262:
1260:Steric effects
1257:
1252:
1247:
1242:
1237:
1232:
1227:
1222:
1217:
1212:
1207:
1202:
1197:
1192:
1187:
1182:
1177:
1172:
1167:
1162:
1157:
1152:
1147:
1142:
1137:
1132:
1127:
1122:
1117:
1112:
1107:
1102:
1097:
1092:
1087:
1082:
1077:
1072:
1067:
1062:
1057:
1052:
1047:
1042:
1037:
1032:
1027:
1022:
1017:
1012:
1007:
1002:
997:
992:
987:
982:
977:
972:
967:
962:
957:
952:
947:
941:
938:
937:
935:
934:
929:
924:
919:
914:
912:Redox reaction
909:
904:
899:
897:Polymerization
894:
889:
883:
880:
879:
871:
870:
863:
856:
848:
840:
839:
803:
750:
723:
712:(4): 951–954.
695:
660:
609:
596:(5): 276–284.
573:
542:
531:(4): 704–723.
515:
496:(2): 146–156.
490:Chem. Soc. Rev
480:
474:978-0471264187
473:
447:
440:
421:
420:
418:
415:
414:
413:
408:
403:
396:
393:
354:Boyer reaction
349:
341:
338:
314:
310:
228:carbon dioxide
205:hydrazoic acid
199:obtained from
173:
170:
136:hydrazoic acid
98:reacts with a
78:
77:
74:
73:
66:
59:
58:
51:
47:
46:
42:
41:
36:
35:Reaction type
32:
31:
28:
24:
23:
15:
9:
6:
4:
3:
2:
4185:
4174:
4171:
4169:
4166:
4164:
4161:
4160:
4158:
4135:
4132:
4130:
4127:
4125:
4122:
4120:
4117:
4115:
4112:
4110:
4107:
4105:
4102:
4100:
4097:
4095:
4092:
4090:
4087:
4085:
4082:
4080:
4077:
4075:
4072:
4070:
4067:
4065:
4062:
4060:
4057:
4055:
4054:Herz reaction
4052:
4050:
4047:
4045:
4042:
4040:
4037:
4035:
4032:
4030:
4027:
4025:
4022:
4020:
4017:
4015:
4012:
4010:
4007:
4005:
4002:
4000:
3997:
3995:
3992:
3990:
3987:
3985:
3982:
3980:
3977:
3975:
3972:
3970:
3967:
3965:
3962:
3960:
3957:
3955:
3952:
3950:
3947:
3945:
3942:
3940:
3937:
3935:
3932:
3931:
3929:
3925:
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:
3816:
3814:
3811:
3809:
3806:
3804:
3801:
3799:
3796:
3794:
3791:
3789:
3786:
3784:
3781:
3779:
3776:
3774:
3771:
3769:
3766:
3764:
3761:
3760:
3758:
3756:
3755:Cycloaddition
3752:
3746:
3743:
3741:
3738:
3736:
3733:
3731:
3728:
3726:
3723:
3721:
3718:
3716:
3713:
3711:
3708:
3706:
3703:
3701:
3698:
3696:
3693:
3691:
3688:
3686:
3683:
3681:
3678:
3676:
3673:
3671:
3668:
3666:
3663:
3661:
3658:
3656:
3653:
3651:
3648:
3646:
3643:
3641:
3638:
3636:
3633:
3631:
3628:
3626:
3623:
3621:
3618:
3616:
3613:
3611:
3608:
3606:
3603:
3601:
3600:Isay reaction
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:
3495:Cycloaddition
3493:
3491:
3488:
3486:
3483:
3481:
3478:
3476:
3473:
3471:
3468:
3466:
3463:
3461:
3458:
3456:
3453:
3451:
3448:
3446:
3443:
3441:
3438:
3436:
3433:
3431:
3428:
3426:
3423:
3421:
3418:
3416:
3413:
3411:
3408:
3406:
3403:
3401:
3398:
3397:
3395:
3393:
3390:Ring forming
3387:
3381:
3378:
3376:
3373:
3371:
3368:
3366:
3363:
3361:
3358:
3356:
3353:
3351:
3348:
3346:
3343:
3341:
3338:
3336:
3333:
3331:
3328:
3326:
3323:
3321:
3318:
3316:
3313:
3311:
3308:
3306:
3303:
3301:
3298:
3296:
3293:
3291:
3290:Rupe reaction
3288:
3286:
3283:
3281:
3278:
3276:
3273:
3271:
3268:
3266:
3263:
3261:
3258:
3256:
3253:
3251:
3248:
3246:
3243:
3241:
3238:
3236:
3233:
3231:
3228:
3226:
3223:
3221:
3218:
3216:
3213:
3211:
3208:
3206:
3203:
3201:
3198:
3196:
3193:
3191:
3188:
3186:
3183:
3181:
3178:
3176:
3173:
3171:
3168:
3166:
3163:
3161:
3158:
3156:
3153:
3151:
3148:
3146:
3143:
3141:
3138:
3136:
3133:
3131:
3128:
3126:
3123:
3121:
3118:
3116:
3113:
3111:
3108:
3106:
3103:
3101:
3098:
3096:
3093:
3091:
3088:
3086:
3083:
3081:
3078:
3076:
3073:
3071:
3068:
3066:
3063:
3061:
3058:
3056:
3053:
3051:
3048:
3046:
3043:
3041:
3038:
3036:
3033:
3031:
3028:
3026:
3023:
3021:
3018:
3016:
3013:
3011:
3008:
3006:
3003:
3001:
2998:
2996:
2993:
2991:
2988:
2986:
2983:
2981:
2978:
2976:
2973:
2971:
2968:
2966:
2963:
2961:
2958:
2956:
2953:
2951:
2948:
2946:
2943:
2941:
2938:
2936:
2933:
2931:
2928:
2926:
2923:
2921:
2918:
2916:
2913:
2912:
2910:
2908:
2902:
2896:
2893:
2891:
2888:
2886:
2883:
2881:
2878:
2876:
2873:
2871:
2868:
2866:
2863:
2861:
2858:
2856:
2853:
2851:
2848:
2846:
2843:
2841:
2838:
2836:
2833:
2831:
2828:
2826:
2823:
2821:
2818:
2816:
2813:
2811:
2808:
2806:
2803:
2801:
2798:
2796:
2793:
2791:
2788:
2786:
2783:
2781:
2778:
2776:
2773:
2771:
2768:
2766:
2763:
2761:
2758:
2756:
2753:
2751:
2748:
2746:
2743:
2741:
2738:
2736:
2733:
2731:
2728:
2726:
2723:
2721:
2718:
2716:
2713:
2711:
2708:
2706:
2703:
2701:
2698:
2696:
2693:
2691:
2688:
2686:
2683:
2681:
2680:Ley oxidation
2678:
2676:
2673:
2671:
2668:
2666:
2663:
2661:
2658:
2656:
2653:
2651:
2648:
2646:
2645:Hydroxylation
2643:
2641:
2638:
2636:
2635:Hydrogenation
2633:
2631:
2628:
2626:
2623:
2621:
2618:
2616:
2613:
2611:
2608:
2606:
2603:
2601:
2598:
2596:
2593:
2591:
2588:
2586:
2583:
2581:
2578:
2576:
2573:
2571:
2570:DNA oxidation
2568:
2566:
2563:
2561:
2560:Deoxygenation
2558:
2556:
2553:
2551:
2548:
2546:
2543:
2541:
2538:
2536:
2533:
2531:
2528:
2526:
2523:
2521:
2518:
2516:
2513:
2511:
2508:
2506:
2503:
2501:
2498:
2496:
2493:
2491:
2488:
2486:
2483:
2481:
2478:
2476:
2473:
2471:
2468:
2466:
2463:
2461:
2458:
2456:
2453:
2451:
2450:Aromatization
2448:
2446:
2443:
2441:
2438:
2436:
2433:
2431:
2428:
2426:
2423:
2421:
2418:
2416:
2413:
2411:
2408:
2407:
2405:
2403:
2397:
2391:
2388:
2386:
2383:
2381:
2378:
2376:
2373:
2371:
2368:
2366:
2363:
2361:
2358:
2356:
2353:
2351:
2348:
2346:
2343:
2341:
2338:
2336:
2333:
2331:
2328:
2326:
2323:
2322:
2320:
2314:
2308:
2305:
2303:
2300:
2298:
2295:
2293:
2290:
2288:
2287:Reed reaction
2285:
2283:
2280:
2278:
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:
2204:
2202:
2198:bond forming
2194:
2184:
2181:
2179:
2176:
2174:
2171:
2169:
2166:
2164:
2161:
2159:
2156:
2154:
2151:
2149:
2146:
2144:
2141:
2139:
2136:
2134:
2131:
2129:
2126:
2124:
2121:
2119:
2116:
2114:
2111:
2109:
2106:
2104:
2103:Cope reaction
2101:
2099:
2096:
2094:
2091:
2089:
2086:
2084:
2081:
2080:
2078:
2074:
2068:
2065:
2063:
2060:
2058:
2055:
2053:
2050:
2048:
2045:
2043:
2040:
2038:
2035:
2034:
2032:
2030:
2026:
2020:
2017:
2015:
2012:
2010:
2007:
2005:
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:
1920:
1917:
1915:
1912:
1910:
1907:
1905:
1902:
1900:
1897:
1895:
1892:
1890:
1887:
1885:
1882:
1880:
1877:
1875:
1872:
1870:
1867:
1865:
1862:
1860:
1857:
1855:
1852:
1850:
1847:
1845:
1842:
1840:
1837:
1835:
1832:
1830:
1827:
1825:
1822:
1820:
1817:
1815:
1814:Nef synthesis
1812:
1810:
1807:
1805:
1802:
1800:
1797:
1795:
1792:
1790:
1789:Methylenation
1787:
1785:
1782:
1780:
1777:
1775:
1772:
1770:
1767:
1765:
1762:
1760:
1757:
1755:
1752:
1750:
1747:
1745:
1742:
1740:
1737:
1735:
1732:
1730:
1727:
1725:
1722:
1720:
1717:
1715:
1712:
1710:
1707:
1705:
1702:
1700:
1697:
1695:
1692:
1690:
1687:
1685:
1682:
1680:
1677:
1675:
1672:
1670:
1667:
1665:
1662:
1660:
1659:Heck reaction
1657:
1655:
1652:
1650:
1647:
1645:
1642:
1640:
1637:
1635:
1632:
1630:
1627:
1625:
1622:
1620:
1617:
1615:
1612:
1610:
1607:
1605:
1602:
1600:
1597:
1595:
1592:
1590:
1587:
1585:
1582:
1580:
1577:
1575:
1572:
1570:
1567:
1565:
1562:
1560:
1557:
1555:
1552:
1550:
1547:
1545:
1542:
1540:
1537:
1535:
1532:
1530:
1527:
1525:
1522:
1520:
1517:
1515:
1512:
1510:
1507:
1505:
1502:
1500:
1497:
1495:
1492:
1490:
1487:
1485:
1482:
1480:
1477:
1475:
1472:
1470:
1467:
1465:
1462:
1460:
1457:
1455:
1452:
1450:
1447:
1445:
1442:
1440:
1437:
1435:
1432:
1430:
1427:
1425:
1422:
1420:
1417:
1415:
1412:
1410:
1407:
1405:
1402:
1400:
1397:
1395:
1392:
1390:
1387:
1385:
1382:
1380:
1377:
1375:
1372:
1370:
1367:
1365:
1362:
1360:
1357:
1355:
1352:
1350:
1347:
1346:
1344:
1340:bond forming
1336:
1332:
1327:
1321:
1318:
1316:
1313:
1311:
1308:
1306:
1305:Y-aromaticity
1303:
1301:
1298:
1296:
1293:
1291:
1290:Walsh diagram
1288:
1286:
1283:
1281:
1278:
1276:
1275:Taft equation
1273:
1271:
1268:
1266:
1263:
1261:
1258:
1256:
1253:
1251:
1248:
1246:
1245:ÎŁ-aromaticity
1243:
1241:
1238:
1236:
1233:
1231:
1228:
1226:
1223:
1221:
1218:
1216:
1213:
1211:
1208:
1206:
1203:
1201:
1198:
1196:
1193:
1191:
1188:
1186:
1183:
1181:
1178:
1176:
1173:
1171:
1170:Marcus theory
1168:
1166:
1163:
1161:
1158:
1156:
1153:
1151:
1148:
1146:
1145:HĂĽckel's rule
1143:
1141:
1138:
1136:
1133:
1131:
1128:
1126:
1123:
1121:
1118:
1116:
1113:
1111:
1108:
1106:
1103:
1101:
1100:Evelyn effect
1098:
1096:
1093:
1091:
1088:
1086:
1083:
1081:
1080:Electron-rich
1078:
1076:
1073:
1071:
1068:
1066:
1063:
1061:
1058:
1056:
1053:
1051:
1048:
1046:
1043:
1041:
1038:
1036:
1033:
1031:
1028:
1026:
1023:
1021:
1018:
1016:
1013:
1011:
1008:
1006:
1003:
1001:
998:
996:
995:Bema Hapothle
993:
991:
988:
986:
983:
981:
978:
976:
973:
971:
968:
966:
963:
961:
958:
956:
953:
951:
948:
946:
943:
942:
939:
933:
930:
928:
925:
923:
920:
918:
915:
913:
910:
908:
905:
903:
900:
898:
895:
893:
890:
888:
885:
884:
881:
877:
869:
864:
862:
857:
855:
850:
849:
846:
835:
831:
827:
823:
819:
815:
807:
799:
795:
790:
785:
781:
777:
773:
770:
769:
761:
754:
746:
742:
738:
734:
727:
719:
715:
711:
708:
707:
699:
691:
687:
683:
679:
675:
671:
664:
656:
652:
648:
644:
640:
636:
632:
628:
624:
620:
613:
604:
599:
595:
591:
587:
580:
578:
569:
565:
561:
558:
557:
549:
547:
538:
534:
530:
526:
519:
511:
507:
503:
499:
495:
491:
484:
476:
470:
466:
462:
458:
451:
443:
441:0-470-01041-X
437:
433:
426:
422:
412:
409:
407:
404:
402:
399:
398:
388:
384:
382:
378:
374:
365:
361:
359:
355:
347:
337:
330:
326:
324:
320:
308:
304:
300:
296:
292:
288:
284:
281:of the final
280:
276:
272:
268:
264:
260:
256:
252:
248:
239:
235:
233:
229:
225:
222:
218:
214:
210:
206:
202:
198:
194:
189:
187:
186:sulfuric acid
183:
179:
166:
159:
155:
153:
149:
145:
141:
137:
133:
129:
125:
121:
117:
113:
109:
105:
101:
97:
93:
89:
85:
75:
71:
67:
64:
61:
60:
56:
52:
49:
48:
43:
40:
37:
34:
33:
29:
26:
25:
20:
3294:
3095:Ene reaction
2455:Autoxidation
2316:Degradation
2207:Azo coupling
1984:Ugi reaction
1584:Ene reaction
1384:Alkynylation
1235:Polyfluorene
1230:Polar effect
1095:Electrophile
1010:Bredt's rule
980:Baird's rule
950:Alpha effect
817:
813:
806:
771:
766:
753:
736:
732:
726:
709:
704:
698:
673:
669:
663:
622:
618:
612:
593:
589:
559:
554:
528:
524:
518:
493:
489:
483:
456:
450:
431:
425:
370:
353:
343:
335:
318:
306:
302:
298:
290:
286:
274:
270:
265:, as in the
262:
254:
244:
223:
208:
196:
190:
175:
132:benzophenone
94:in which an
87:
81:
70:RXNO:0000170
65:ontology ID
45:Identifiers
27:Named after
1594:Ethenolysis
1240:Ring strain
1210:Nucleophile
1035:Clar's rule
975:Aromaticity
459:: 307–336.
323:α-tetralone
201:protonation
140:benzanilide
4157:Categories
3878:Ozonolysis
3405:Annulation
2755:Ozonolysis
874:Topics in
676:(2): 211.
417:References
373:annulation
217:isocyanate
3392:reactions
2907:reactions
2402:reactions
2318:reactions
2200:reactions
1342:reactions
690:0004-9425
655:250898289
647:0036-021X
381:alkaloids
221:carbamate
1285:Vinylogy
955:Annulene
902:Reagents
834:15113219
798:17302421
510:16444296
395:See also
305:to give
279:tautomer
124:nitrogen
104:aldehyde
100:carbonyl
945:A value
789:2596723
627:Bibcode
377:lactams
247:ketones
230:to the
193:acylium
152:ketones
832:
796:
786:
688:
653:
645:
508:
471:
438:
346:azides
142:. The
108:ketone
90:is an
86:, the
651:S2CID
283:amide
232:amine
120:amide
116:amine
110:, or
96:azide
830:PMID
794:PMID
686:ISSN
643:ISSN
506:PMID
469:ISBN
436:ISBN
379:and
195:ion
134:and
822:doi
818:126
784:PMC
776:doi
772:129
741:doi
737:117
714:doi
678:doi
635:doi
598:doi
564:doi
560:113
533:doi
498:doi
461:doi
348:R-N
138:to
118:or
82:In
63:RSC
4159::
828:.
816:.
792:.
782:.
765:.
735:.
710:77
684:.
674:63
672:.
649:.
641:.
633:.
623:47
621:.
594:60
592:.
588:.
576:^
545:^
529:57
527:.
504:.
494:35
492:.
467:.
383:.
313:SO
299:10
234:.
106:,
867:e
860:t
853:v
836:.
824::
800:.
778::
747:.
743::
720:.
716::
692:.
680::
657:.
637::
629::
606:.
600::
570:.
566::
539:.
535::
512:.
500::
477:.
463::
444:.
350:3
319:9
315:4
311:2
307:5
303:3
291:3
287:9
275:7
271:6
263:6
255:3
224:4
209:2
197:1
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