CARBON-CARBON BOND FORMATION AND KETENIMINE SYNTHESIS FROM N-PHENYL IMIDOTHIOESTERS

N Lage, S Masson, A Thuillier

Index: Lage, Nadia; Masson, Serge; Thuillier, Andre Phosphorus, Sulfur and Silicon and the Related Elements, 1991 , vol. 59, # 1-4 p. 141 - 144

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Citation Number: 4

Abstract

Abstract Methyl N-phenyl ethanimidothioate 1 and its α-silylated homologue 2 are metallated into lithiated enaminates which can be regioselectively mono-alkylated at-78° C on the α-carbon atom. Imidothioester 2, treated at higher temperatures by 2 equivalents of Buli, leads, after alkylation or hydrolysis, to stable silylated N-phenyl ketenimines. Formation of ketenimines are also observed by flash thermolysis of 2 or of the silylated S, N-ketene ...