Isothiocyanates from Tosyl Chloride Mediated Decomposition of in Situ Generated Dithiocarbamic Acid Salts
- 20 April 2007
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 72 (10), 3969-3971
- https://doi.org/10.1021/jo070246n
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.Keywords
This publication has 5 references indexed in Scilit:
- Superior Reactivity of Thiosemicarbazides in the Synthesis of 2-Amino-1,3,4-oxadiazolesThe Journal of Organic Chemistry, 2006
- Isothiocyanates in the chemistry of heterocyclesChemical Reviews, 1991
- The Modified Kaluza Synthesis. III. The Synthesis of Some Aromatic IsothiocyanatesThe Journal of Organic Chemistry, 1964
- The Synthesis of Isothiocyanates from AminesThe Journal of Organic Chemistry, 1956
- NITRO AND AMINO TRIPHENYLGUANIDINES1Journal of the American Chemical Society, 1932