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 ...
