Tetrahedron

Tandem Wolff rearrangement-“tert-amino effect” sequence: Synthesis of 2-oxoindolinium enolate derivatives

F Léost, B Chantegrel, C Deshayes

Index: Leost, Francoise; Chantegrel, Bernard; Deshayes, Christian Tetrahedron, 1997 , vol. 53, # 22 p. 7557 - 7576

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Citation Number: 16

Abstract

The thermolysis of 1-diazo-2-oxo-(2-N, N-disubstituted aminophenyl) ethylphosphonates 1 gave rise to 2-oxoindolinium enolate derivatives 4 through Wolff rearrangement and interaction of the tert-amino moiety with the ketene functionality. Variable amounts of either ammonium ylides 5 or of products resulting from their transformations were also formed during the course of the reaction. If the amino moiety was substituted by a benzyl or an ...