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J Org Chem. 2007 May 11;72(10):3969-71. Epub 2007 Apr 20.

Isothiocyanates from tosyl chloride mediated decomposition of in situ generated dithiocarbamic acid salts.

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1
Department of Process Research, Merck Frosst Centre for Therapeutic Research, 16711 route transcanadienne, Kirkland, Qu├ębec, Canada H9H 3L1.

Abstract

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.

PMID:
17444687
DOI:
10.1021/jo070246n
[Indexed for MEDLINE]
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