Homogeneous and Stereoselective Copper (II)-Catalyzed Monohydration of Methylenemalononitriles to 2-Cyanoacrylamides

X Xin, D Xiang, J Yang, Q Zhang, F Zhou…

Index: Xin, Xiaoqing; Xiang, Dexuan; Yang, Jiming; Zhang, Qian; Zhou, Fenguo; Dong, Dewen Journal of Organic Chemistry, 2013 , vol. 78, # 23 p. 11956 - 11961

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Citation Number: 7

Abstract

A facile and efficient route for the homogeneous and highly stereoselective monohydration of substituted methylenemalononitriles to (E)-2-cyanoacrylamides catalyzed by copper (II) acetate monohydrate in acetic acid containing 2% water is described, and a mechanism is proposed. The protocol has proved to be suitable for the monohydration of dicyanobenzenes and 2-substituted malononitriles.