Electroorganic chemistry. 99.. beta.-Acetoxylation and. beta.-halogenation of N-methoxycarbonyl cyclic amines

T Shono, Y Matsumura, O Onomura…

Index: Shono, Tatsuya; Matsumura, Yoshihiro; Onomura, Osamu; Ogaki, Masaru; Kanazawa, Takenobu Journal of Organic Chemistry, 1987 , vol. 52, # 4 p. 536 - 541

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Citation Number: 46

Abstract

Anodic oxidation of N (methoxycarbony1) pyrrolidines (n= 1) and-piperidines (n= 2)(A) gave a,@-disubstituted compounds B, in which the a-substituent was an acetoxy, hydroxy, or methoxy group and the@-substituent was an acetoxy group or halogen atom. The a- substituents of B were easily removed by NaBH4 under acidic conditions to give@- substituted compounds C. A reaction mechanism involving the formation of a,@- ...