The geometry of displacements at nonstereogenic atoms: the formal displacement of alkoxide from alkoxyamines by organolithium reagents

P Beak, A Basha, B Kokko, DK Loo

Index: Beak, Peter; Basha, Anwer; Kokko, Bruce; Loo, DeKai Journal of the American Chemical Society, 1986 , vol. 108, # 19 p. 6016 - 6023

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Citation Number: 63

Abstract

Abstract: Amination of organolithium reagents can be achieved by reaction with methyllithium-alkoxyamines. Details of the methodology and analysis of the reaction mechanism are presented. Reactions of methyl-, ethyl-, n-butyl-, sec-butyl-, tert-butyl-, phenyl-, and (o" thoxypheny1) lithium with methyllithium-methoxyamine give the corresponding amines, isolated as the benzamides, in yields of 71-97%. Lower yields are ...