Isothiocyanates from Tosyl Chloride Mediated Decomposition of in Situ Generated Dithiocarbamic Acid Salts

Rince Wong and Sarah J. Dolman*
Department of Process Research, Merck Frosst Centre for Therapeutic Research, 16711 route transcanadienne, Kirkland, Qubec, Canada H9H 3L1 sarah_dolman@merck.com
J. Org. Chem., 2007, 72 (10), pp 3969–3971
DOI: 10.1021/jo070246n
Publication Date (Web): April 20, 2007
Copyright © 2007 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

Abstract Image

A facile and general protocol for the preparation of isothiocyanates from alkyl and aryl amines is reported. This method relies on a tosyl chloride mediated decomposition of a dithiocarbamate salt that is generated in situ by treatment of an amine with carbon disulfide and triethylamine. Utilizing this protocol, we have prepared 19-alkyl- and arylisothiocyanates in moderate to excellent yield.

Tools

History

  • Published In Issue May 11, 2007
  • Received February 5, 2007

Recommend & Share

Related Content

Other ACS content by these authors: