The Journal of Organic Chemistry

Reactions of N-halobenzylalkylamines with sodium methoxide in methanol

BR Cho, JC Yoon, RA Bartsch

Index: Cho, Bong Rae; Yoon, Jong Chan; Bartsch, Richard A. Journal of Organic Chemistry, 1985 , vol. 50, # 24 p. 4943 - 4946

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Citation Number: 8

Abstract

Reactions of N-halobenzylmethylamines 1 and 2 (X= C1 and Br) with MeONa-MeOH have been investigated. Eliminations from 1 were quantitative, producing only benzylidenemethylamines. Reaction of 2 with MeONa-MeOH produced benzylidenemethylamines and benzylmethylamines. The yield of benzylidenemethylamine increased with electron-withdrawing aryl substituents and increased base concentration ...