100428-85-1Relevant articles and documents
A practical solution for aqueous reactions of water-insoluble high-melting-point organic substrates
Cui, Xiaoxue,Li, Bo,Liu, Tianzhen,Li, Chunbao
supporting information; experimental part, p. 668 - 672 (2012/06/01)
A practical solution to the problem of performing aqueous reactions for very sparingly soluble high-melting-point (VSSHMP) organic substrates has been developed, which entails mechanically stirring a mixture of the substrate, the corresponding reagent(s), water, catalytic Aliquat 336 and sand. When the melting points of the substrates which include steroids, ketones, aldehydes, aromatics and alkaloids are around 200 °C, the reactions can be performed at 20 °C. The substrate solubility can be as low as 1 × 10-10 mol L-1. The Royal Society of Chemistry 2012.
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.
