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

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

The Journal of organic chemistry (2007-04-21)
Rince Wong, Sarah J Dolman
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
p-Toluenesulfonyl chloride, ReagentPlus®, ≥99%
Sigma-Aldrich
p-Toluenesulfonyl chloride, reagent grade, ≥98%