Isothiocyanates from tosyl chloride mediated decomposition of in situ generated dithiocarbamic acid salts.
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.
Wong
Rince
R
Department of Process Research, Merck Frosst Centre for Therapeutic Research, 16711 route transcanadienne, Kirkland, Québec, Canada H9H 3L1.
Dolman
Sarah J
SJ
D000588:Amines / Q000737:chemistry; D017879:Isothiocyanates / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013859:Thiocarbamates / Q000138:chemical synthesis / Q000737:chemistry*; D014105:Tosyl Compounds / Q000737:chemistry*
D000588:Amines; D017879:Isothiocyanates; D013859:Thiocarbamates; D014105:Tosyl Compounds; C025506:4-toluenesulfonyl chloride