New synthesis of propargylic amines from 2-(bromomethyl) aziridines. Intermediacy of 3-bromoazetidinium salts

M D'hooghe, W Van Brabandt…

Index: D'Hooghe, Matthias; Van Brabandt, Willem; De Kimpe, Norbert Journal of Organic Chemistry, 2004 , vol. 69, # 8 p. 2703 - 2710

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Citation Number: 45

Abstract

A new, efficient, and straightforward synthesis provides propargylamines in high overall yields (64-77%) by transformation of 1-(arylmethyl)-2-(bromomethyl) aziridines into N, N-di (arylmethyl)-N-(2-propynyl) amines via N-(2, 3-dibromopropyl) amines and N-(2-bromo-2- propenyl) amines. The conversion of N-(2, 3-dibromopropyl) amines into N-(2-bromo-2- propenyl) amines is based on a novel analogue of the Hofmann elimination. A Yamaguchi ...

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