The conversion of some carbohydrate diols into cyclic carbonates and thiocarbonates by means of N-dichloromethylene-N,N-dimethylammonium chloride (Viehe's salt)

Abstract

Various carbohydrate cis and trans vicinal diols have been treated with N-dichloromethylene-N,N- dimethylammonium chloride (Viehe's salt), and the resulting cyclic salts quenched with water or sodium hydrogen sulfide to form, in the main, cyclic carbonates and thiocarbonates. These results are discussed in light of the 'orbital-assist' proposal by Deslongchamps.