Tetrahedron letters

The dealkylation of tertiary aliphatic amines with phenyl chlorothionoformate

DS Millan, RH Prager

Index: Millan, David S.; Prager, Rolf H. Tetrahedron Letters, 1998 , vol. 39, # 24 p. 4387 - 4390

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Citation Number: 20

Abstract

Phenyl chlorothionoformate reacts rapidly with aliphatic amines at 20° C to give a thiourethane and an alkyl chloride. The urethanes are readily converted to the secondary amine salt by reaction with dimethyl sulfate, followed by hydrolysis with water. Rates of reaction, and alkyl group cleavage selectivity, are comparable to those reported for 1- chloroethyl chloroformate.