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The dealkylation of tertiary aliphatic amines with phenyl chlorothionoformate

✍ Scribed by David S. Millan; Rolf H. Prager

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 174 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)00743-6

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✦ Synopsis

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.

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