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

Article abstract of DOI:10.1021/jo00380a011

Anodic oxidation of N-(methoxycarbonyl)pyrrolidines (n = 1) and -piperidines (n = 2) (A) gave α,β-disubstituted compounds B, in which the α-substituent was an acetoxy, hydroxy, or methoxy group and the β-substituent was an acetoxy group or halogen atom. The α-substituents of B were easily removed by NaBH₄ under acidic conditions to give β-substituted compounds C. A reaction mechanism involving the formation of α,β-unsaturated intermediate E followed by anodic oxidation of E or attack of halogen-active species on E has been presented for the anodic α,β-disubstitution.