A Convenient, High Yielding Cleavage of the Thiocarbonyl Group in Xanthates

摘要

As part of our ongoing studies on the degenerative radical transfer reactions of xanthates and related derivatives, we required an effective, general, and ecologically acceptable procedure for the cleavage of the thiocarbonyl group in the product and its replacement by a carbonyl. Several procedures have been described in the literature for performing such a transformation. They involve various metal salts such as mercuric acetate, cupric chloride, and silver nitrate, N-bromo- or N-iodosuccini-mide, sodium nitrite/HCl, peracids, singlet oxygen, phenyl-seleninic acid or anhydride, and dianisyl telluroxide. More recently Barba and co-workers accomplished the conversion of a xanthate into a thiolcarbonate by anodic oxidation.