The Journal of Organic Chemistry

Reactions of primary amines with organolithium compounds

HG Richey Jr, WF Erickson

Index: Richey, Herman G.; Erickson, Wayne F. Journal of Organic Chemistry, 1983 , vol. 48, # 23 p. 4349 - 4357

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Citation Number: 13

Abstract

Primary amines react under mild conditions with an excess of an organolithium compound to form imines and a-substituted primary amines. Frequently, N-alkylimines that result from the condensation of these products are also isolated. For example, reactions of PhCHzNHz with RLi (R= n-Bu) in refluxing hexane furnish (after hydrolysis) PhCHRNH2, PhRC= O, PhRC= NCHRPh, and R2C= 0. The organic group of the primary amine can be a primary, ...