Phenyl chloro(thionoformate): a new dealkylating agent of tertiary amines

Phenyl chloro(thionoformate) reacts rapidly with unhindered tertiary alipha tic amines at 20 degrees to give a thiocarbamate and an alkyl chloride. Dia lkylcyclohexylamines react surprisingly rapidly to form predominantly cyclo hexene. The thiocarbamates are converted into the secondary amine salt by t reatment with dimethyl sulfate, followed by hydrolysis with water. Rates of reaction and alkyl group cleavage selectivity in amines were found to be s uperior or comparable to those previously reported with chloroformates.