A Simple and Novel Eco-Friendly Process for the One-Pot Synthesis of Dithiocarbamates from Amines, Carbon Disulfide, and Epoxides

Abstract

An environmentally benign, highly efficient, and simple protocol for the synthesis of various structurally divergent dithiocarbamate derivatives in one-pot reaction of amines, carbon disulfide, and epoxides, without using any solvent and catalyst at room temperature, is presented. This new procedure has the advantages of higher yield, lower cost, reduced environmental impact, and simple work-up procedure.

Catalyst-free, atom-economical and regioselective multicomponent polymerizations of diamines, CS2, and diepoxides toward functional polydithiourethanes

“…The phenomena were consistent with small molecule reactions reported in the literature. [36][37][38][39][40] It is assumed that the in situ generated dithiocarbamic acid predominantly attacks the less hindered methylene of the epoxide to give the specific regioisomer. Meanwhile, in the 13 C NMR spectra of the model compound 5 and P1, the typical dithiocarbamate carbon peak at 197 ppm, the methylene carbon peak 9 connected to N atoms at 50 ppm and the methylene carbon peak 7 adjacent to S atoms at 38 ppm could be observed (Fig.…”

“…The mechanism of this three-component reaction has been well documented in the literature. [36][37][38][39][40] It is assumed that the unstable dithiocarbamic acid, initially generated from the amine and CS 2 , reacts with the epoxide leading to the formation of β-hydroxyl dithiourethane (Scheme S1 †). Moreover, the dithiourethane groups endow the polymers with non-conventional fluorescence properties and heavy metal adsorption ability.…”