Abstract:

Alkyl, aryl and bifunctional isothiocyanates were synthesized in moderate to excellent yields(77%96%) in a two-step and one-pot reaction. The reaction were started with parent primary amines, carbon disulfide in toluene in presence of N,N-diethyl-ethanamine(Et₃N) at room temperature, followed by reaction of the thus formed dithiocarbamates with t-butylcarbonic diethylphoric anhydride(3) from -5 ℃ to room temperature. The best molar ratio of substrates was n(primary amines):n(CS₂):n(Et₃N):n(3)=1:1.1:3.3:1.1. The procedure was quite simple and the substrate scope is broad. This method is compatible with a variety of protecting groups and the chiral center in investigated compounds. Compound 3 was used as an new commericial available safe and efficient desulfurization reagent.

Key words: t-butylcarbonic diethylphoric anhydride, isothiocyanate, primary amine, carbon disulfide, desulfurizing reagent