Metalation-induced migration of phosphorus from nitrogen to carbon

AM Jardine, SM Vather, TA Modro

Index: Jardine, Anwar M.; Vather, Sunil M.; Modro, Tomasz A. Journal of Organic Chemistry, 1988 , vol. 53, # 17 p. 3983 - 3985

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Citation Number: 17

Abstract

Phosphoric N-phenylamides undergo lithiation-induced rearrangement involving the fission of the PN bond and the migration of phosphorus to the ortho aromatic carbon atom. In the 0- phenyl N-phenylamido esters the migration to the phenolic ring preceeds that occurring at the aniline moiety. The reaction is illustrated by the preparation of the ortho-substituted aromatic phosphonic and phosphinic esters, as well as tertiary phosphine oxides. NMR ( ...