Phenyl chloro(thionoformate) reacts rapidly with unhindered tertiary aliphatic amines at 20° to give a thiocarbamate and an alkyl chloride. Dialkylcyclohexylamines react surprisingly rapidly to form predominantly cyclohexene. The thiocarbamates are converted into the secondary amine salt by treatment with dimethyl sulfate, followed by hydrolysis with water. Rates of reaction and alkyl group cleavage selectivity in amines were found to be superior or comparable to those previously reported with chloroformates.

Phenyl chloro(thionoformate) is a rapid and selective dealkylating agent for tertiary aliphatic amines, with rates of reaction and alkyl group cleavage comparable to those of chloroformates.

Paper

Phenyl Chloro(thionoformate): a New Dealkylating Agent of Tertiary Amines

References

Citations