An iodine-potassium t-butoxide catalysed conversion of thioamides and thioureas to their oxygen analogs

Abstract

The title conversion, significant for its role in procuring modified nucleic acids has been reported with bis(p-methoxyphenyl) telluroxide, trimethyloxoniujn fluoborate, DMSO/acids and DMSO/iodine. During the course of investigation of the reactions of heterocycles possessing thiourea and thioamide functionals, with iodocarbene generated from iodoform and potassium t-butoxide, we noticed the conversions of these substrates to their oxygen analogs. Here, we report that the title conversion can be performed in a synthetically useful manner, under basic conditions, with the help of iodine/potassium t-butoxide in t-butanol solution.