RADICAL-BASED DEOXYGENATION OF ALIPHATIC-ALCOHOLS VIA THIOXOCARBAMATE DERIVATIVES

N-Phenylthioxocarbamates, obtained from the reaction of alcohols with phenyl isothiocyanate in the presence of NaH, were reduced with various silanes such as triethylsilane, triphenylsilane, and tris(trimethylsilyl)silane, as well as tributylstannane under radical conditions to give deoxygenated products of the corresponding alcohols in excellent yields. The reaction was applicable to not only simple aliphatic alcohols but also sugars and nucleosides. Regio- and stereoselective deuteration using deuteriosilanes and deuteriostannane was also examined under the similar conditions.