Abstract

o-Nitrophenyl chlorothionoformate reacts readily with unhindered tertiary aliphatic amines in only 10 min at room temperature, and gives the dialkylamine salts after treatment of initial thiocarbamate with dimethyl sulfate followed by hydrolysis with water. The ease of cleavage of alkyl groups from tertiary amines with 4-chlorophenyl chlorothionoformate is benzyl > t-butyl > allyl > methyl and using 2, 4, 6-tribromophenyl chlorothionoformate it is benzyl > allyl > t-butyl > methyl.

Keywords: o-Nitrophenyl chlorothionoformate, benzylic and allylic cleavage of tertiary amines, secondary aliphatic amines from tertiary amines.