Reactions of N-chlorobenzylmethylamines with secondary amines in acetonitrile. Effect of base strength upon the imine-forming transition state

BR Cho, SK Namgoong, RA Bartsch

Index: Cho, Bong Rae; Namgoong, Sung Keon; Bartsch, Richard A. Journal of Organic Chemistry, 1986 , vol. 51, # 8 p. 1320 - 1324

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Citation Number: 16

Abstract

Reactions of N-chlorobenzylmethylamines 1 with R2NH in MeCN have been investigated kinetically. Eliminations from 1 were quantitative and regiospecific, producing only benzylidenemethylamines. For the elimination reaction of 1 with Bu2NH, kH/k,= 8.8, p= 0.96, AH'= 7.6 kcal/mol, and AS*=-45.1 eu were determined. The transition state structure is assessed as being highly symmetrical with similar extents of C,-H and No-C1 bond ...

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