Reactions of N-Halobenzylalkylamines with Sodium Methoxide in Methanol

Bong Rae Cho, Jong Chan Yoon, Richard A. Bartsch

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15 Citations (Scopus)

Abstract

Reactions of N-halobenzylmethylamines 1 and 2 (X = Cl 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 and became quantitative when pentane was used as a solvent. The results are interpreted as competing bimolecular elimination and nucleophilic substitution by methoxide on bromine. Product studies for reaction of NN-halobenzyl-tert-butylamines with MeONa-MeOH and EtSNa-MeOH establish that the substitution reaction is a general reaction pathway available for the N-haloamines. Transition states for eliminations from 1 and 2 are characterized by Hammett p and primary deuterium isotope effect values.

Original languageEnglish
Pages (from-to)4943-4946
Number of pages4
JournalJournal of Organic Chemistry
Volume50
Issue number24
DOIs
Publication statusPublished - 1985 Nov

ASJC Scopus subject areas

  • Organic Chemistry

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