Some aspects of the chemistry of Viehe's salt

[Truncated] N-Dichloromethylene N,N-dimethylamrnonium chloride, 'Viehe's salt,'was investigated as a means of preparing cyclic carbonates and thiocarbonates in carbohydrate molecules. Firstly, the reactions of simple aromatic and aliphatic alcohols and thiols were considered. In most cases the carbonate was obtained in good yield. The intermediate iminium salt formed by reaction of the alcohol or thiolwith Viehe's salt, when treated with sodium hydrogen sulfide, gave the thiocarbonate in good yield. In the case of butanethiol and sodium hydrogen selenide, a dithioselenocarbonate was obtained. This reaction typified the general versatility of the reagent.