89861-51-8Relevant articles and documents
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
Barton, Derek H. R.,Bridon, Dominique,Zard, Samir Z.
, p. 2615 - 2626 (2007/10/02)
Carbon centered radicals obtained by decarboxylative transformation of suitable thiohydroxamate esters react with group Va trisphenylsulphides 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 tris(phenylthio)antimony under air to obtain the nor alcohol directly and in high yield.The intermediate organometalloid could also be oxidised with nitrogen dioxide to give the expected nitroalkane albeit in only modest yield.The corresponding organobismuth intermediate derived from 3,3-diphenylpropionic acid could actually be isolated thereby providing strong evidence for the proposed mechanism.
A Convenient High Yielding Synthesis of Nor-alcohols from Carboxylic Acids
Barton, Derek H. R.,Bridon, Dominique,Zard, Samir Z.
, p. 1066 - 1068 (2007/10/02)
Esters (mixed anhydrides) of carboxylic acids and thiohydroxamic acid (2) react with tris(phenylthio)antimony in the presence of oxygen and water to give high yields of nor-alcohols.
RADICAL CHEMISTRY OF THIOHYDROXAMIC ACID ESTERS
Barton, Derek H. R.,Kretzschmar, Gerhard
, p. 5889 - 5892 (2007/10/02)
Thiohydroxamic esters in general decompose smoothly by a radical chain reaction to give carbon radicals which can be quenched in a synthetically useful manner.