The Journal of Organic Chemistry

The Darzens Condensation. I. Reaction of Chloroacetamides with Acetone and Cyclohexanone

AJ Speziale, HW Frazier

Index: Speziale,A.J.; Frazier,H.W. Journal of Organic Chemistry, 1961 , vol. 26, p. 3176 - 3183

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Citation Number: 8

Abstract

Ethi 1 chloroacetatr undergoes the Darzens condensation with acetone or cyclohexanone regardless of basic agents used. In contrast, N, Y-diethvl-a-chloroacetamide, presumably because of the relatively lower acidity of its a-hydrogens, does not rc, ndily undergo the Darzens condensation. Instead, 7-keto amides are produced as the predominant product. These arise from displacement of the chlorine hv the enolates of acetone and ...