Rearrangement of suitably constituted aryl, alkyl, or vinyl radicals by acyl or cyano group migration

…, DM O'Shea, SW Westwood

文献索引：Beckwith,A.L.; O'Shea,D.M.; Westwood,S.W. Journal of the American Chemical Society, 1988 , vol. 110, p. 2565

被引用次数: 176

摘要

Abstract: Treatment of o-bromobenzyl acetoacetate (14) with tributyltin hydride affords the rearranged product 20 by a mechanism involving 1, 4-acetyl migration in the aryl radical 15 via a cyclic intermediate 16. Similarly, 1, 4-cyano migration in the radical 22 derived from 21 affords rearranged product 24. However, radicals, eg, 26, derived from cyclic keto esters give products formed both by l,. l-acyl migration and by H-atom transfer followed by 1, 2- ...

~15%

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~14%

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~5%

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~9%

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~70%

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~75%

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~75%

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~72%

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