Tetrahedron

Unprecedented formation of stable ketene-N, O-acetals and their rearrangement under basic conditions

M Breuning, T Häuser

Index: Breuning, Matthias; Haeuser, Tobias Tetrahedron, 2007 , vol. 63, # 4 p. 934 - 940

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Citation Number: 2

Abstract

Treatment of 2, 4-disubstituted glutaryl dichlorides with benzimidic acid ethyl ester hydrochloride in the presence of triethylamine did not give the expected bis (acylbenzimidates), but delivered O-acyl-N-ethoxybenzylidene-ketene-N, O-acetals in good to excellent yields. These compounds, which are stable to moisture and chromatography on silica gel, underwent an unprecedented rearrangement to cyclic enamides under stronger ...