The Journal of Organic Chemistry

Palladium-Catalyzed Isomerization of Aryl-Substituted Epoxides: A Selective Synthesis of Substituted Benzylic Aldehydes and Ketones

S Kulasegaram, RJ Kulawiec

Index: Kulasegaram, Sanjitha; Kulawiec, Robert J. Journal of Organic Chemistry, 1997 , vol. 62, # 19 p. 6547 - 6561

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Citation Number: 82

Abstract

Aryl-substituted epoxides bearing multiple methyl substituents on the epoxide ring isomerize in the presence of 5 mol% Pd (OAc) 2/PR3 (R= n-Bu, Ph) to form the corresponding benzylic aldehyde or ketone, with complete regioselectivity for the carbonyl compound formed via cleavage of the benzylic CO bond. No allylic alcohols or products arising from alkyl migration are observed. Rapid reaction rates and nearly quantitative yields are obtained, ...