Organocatalytic CS2 insertion into epoxides in neat conditions: a straightforward approach for the efficient synthesis of Di- and tri-thiocarbonates†

Abstract

The straightforward organocatalytic insertion of carbon disulfide (CS₂) into epoxides using either choline chloride (ChCl) or tetrabutylammonium chloride (TBACl) is reported, for the first time, under solvent-free (neat) conditions. Fine-tuning of our system allowed us to obtain either dithiocarbonates (DTCs) or trithiocarbonates (TTCs) with high efficiency. Additionally, a mechanistic proposal is presented, supported by experimental evidence, DFT calculations and wavefunction analyses.