The reaction of N-dichloromethylene-N,N-dimethylammonium chloride (Viehe's salt) with some carbohydrate diols

Abstract

The reaction of Viehe's salt (Me₂N⁺=CCl₂Cl^-) with various carbohydrate diols (manno, allo) in the presence of a base is reported, the products being, after hydrolysis, either carbonate (with pyridine) or the carbamate (with triethylamine). A rationalization of the two different types of product formed is given in terms of the stereoelectronic control proposal by Deslongchamps.