The Journal of Organic Chemistry

The reaction of oxalyl chloride with amides. II. Oxazolidinediones and acyl isocyanates

AJ Speziale, LR Smith

Index: Speziale,A.J.; Smith,L.R. Journal of Organic Chemistry, 1963 , vol. 28, p. 1805 - 1811

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Citation Number: 106

Abstract

The reaction of oxalyl chloride with N-monosubstituted amides has been shown to yield aryloxamic arid chlorides or 2-methyleneoxazolidine-4, 5-diones depending on the structure of the amide and experimental conditions. Treatment of primary amides with oxalyl chloride was found to be a general preparation of acyl isocyanates. A mechanism for the reaction of oxalyl chloride with various amides is discussed.