The invention of radical reactions. Part XVIII. Decarboxylative radical addition to arsenic, antimony, and bismuth phenylsulphides - a novel synthesis of nor-alcohols from carboxylic acids
作者:Derek H.R. Barton、Dominique Bridon、Samir Z. Zard
DOI:10.1016/s0040-4020(01)80092-2
日期:1989.1
Carbon centered radicals obtained by decarboxylative transformation of suitable thiohydroxamate esters react with group Va trisphenyl-sulphides to give intermediates of general formula R-M(SPh)2 (M = As, Sb, Bi). These react spontaneously with air to give the corresponding alcohols. This procedure is especially useful in the case where M=Sb. It is thus sufficient to stir the thiohydroxamate ester with
A convenient high yielding synthesis of nor-alcohols from carboxylic acids
作者:Derek H. R. Barton、Dominique Bridon、Samir Z. Zard
DOI:10.1039/c39850001066
日期:——
Esters (mixed anhydrides) of carboxylicacids and thiohydroxamic acid (2) react with tris(phenylthio)antimony in the presence of oxygen and water to give high yields of nor-alcohols.
Radicals formed from the esters of thiohydroxamic acids readily add to electron deficient olefins to give adducts of potential synthetic value in variable yield. In certain cases the added sulphur function is easily eliminated with reformation of olefin.