African Journal of
Pure and Applied Chemistry

  • Abbreviation: Afr. J. Pure Appl. Chem.
  • Language: English
  • ISSN: 1996-0840
  • DOI: 10.5897/AJPAC
  • Start Year: 2007
  • Published Articles: 353

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
Email: [email protected]

  •  Accepted: 23 June 2008
  •  Published: 31 July 2008

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.