Categories: C=N Bond Formation >
Synthesis of isothiocyanates
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.
R. Wong, S. J. Dolman, J. Org. Chem., 2007, 72, 3969-3971.
A two-step, one-pot reaction of primary amines or their salts with carbon disulfide, followed by reaction of the intermediate dithiocarbamates with T3P provides isothiocyanates in good yields. T3P® (propane phosphonic acid anhydride) acts as an efficient desulfurating agent.
Ł Janczewski, A. Gajda, S. Frankowski, T. M. Goszczyński, T. Gajda, Synthesis, 2018, 50, 1141-1151.
A facile and efficient synthesis of isothiocyanates involves the reaction of amines with phenyl chlorothionoformate in the presence of solid sodium hydroxide by either a one-pot process or a two-step approach. The one-pot process is useful for preparing alkyl and electron-rich aryl isothiocyanates, whereas the two-step approach is more versatile.
Z.-Y. Li, H.-Z. Ma, C. Han, H.-T. Xi, Q. Meng, X. Chen, X.-Q. Sun, Synthesis, 2013, 45, 1667-1674.