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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, Québec, Canada H9H 3L1, Email:

R. Wong, S. J. Dolman, J. Org. Chem., 2007, 72, 3969-3971.

DOI: 10.1021/jo070246n


A facile and general protocol for the preparation of isothiocyanates from alkyl and aryl amines relies on a tosyl chloride mediated decomposition of a dithiocarbamate salts that are generated in situ by treatment of amines with carbon disulfide and triethylamine. Vairous alkyl- and arylisothiocyanates have been prepared in good yield.

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ID: J42-Y2007-1490