The Journal of Organic Chemistry

Pseudohalogens. X. Effect of some electronic or steric factors on the addition of N, N-dichlorourethane to unsaturated compounds

TA Foglia, D Swern

Index: Foglia,T.A.; Swern,D. Journal of Organic Chemistry, 1968 , vol. 33, # 2 p. 766 - 771

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Citation Number: 22

Abstract

The addition of N, N-dichlorourethan (DCU) to unsaturated compounds with special electronic or steric factors has been investigated. Yields of 8-chlorocarbamates range from 35 to 80%. Electron-withdrawing groups slow down the addition reaction; extensive electron withdrawal completely arrests it. Perfluorocyclohexene, ethyl vinyl sulfone, and diethyl maleate do not react. Addition of DCU to substituted alkenes is subject to steric retardation ...