Journal of Organic Chemistry p. 536 - 541 (1987)
Update date:2022-08-30
Topics:
Shono, Tatsuya
Matsumura, Yoshihiro
Onomura, Osamu
Ogaki, Masaru
Kanazawa, Takenobu
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.
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