Bismuth(III) nitrate pentahydrate: a convenient and selective reagent for conversion of thiocarbonyls to their carbonyl compounds

A variety of thioamides and thioureas are rapidly transformed to their oxo derivatives with Bi(NO3)(3).5H(2)O in excellent yields. However, thiono esters and thioketones are converted to their corresponding carbonyl compounds in only poor yields. Bi(NO3)(3).5H(2)O is relatively non-toxic, insensitive to air and inexpensive. These features coupled with the selective deprotection of thioamides and thioureas in the presence of thiono esters and thioketones make this method an attractive alternative to the existing routes for deprotection of thiocarbonyl compounds. (C) 2002 Elsevier Science Ltd. All rights reserved.