African Journal of Chemistry

African Journal of Chemistry ISSN 4391-3199 Vol. 5 (2), pp. 308-312, February, 2018. © International Scholars Journals

Full Length Research Paper 

The study of reactivity and selectivity of tertiary amines with aryl chlorothionoformates

Masomeh Aghazadeh, Arash Afghan and Mehdi M. Baradarani*

Department of Chemistry, Faculty of Science, University of Urmia, Urmia 57135, Iran.

Accepted 23 October, 2017

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.