Tetrahedron

The invention of new radical chain reactions. part X: High yield radical addition reactions of αβ-unsaturated nitroolefins. An expedient construction of the 25-hydroxy- …

DHR Barton, H Togo, SZ Zard

Index: Barton, Derek H.R.; Togo, Hideo; Zard, Samir Z. Tetrahedron, 1985 , vol. 41, # 23 p. 5507 - 5516

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Citation Number: 78

Abstract

Radicals derived from thiohydroxamic esters 3 readily add to nitroolefins 5 (Z= NO2) to give good yields of α-nitrosulphides. These adducts, where the structure permits, are easily oxidised to carboxylic acids 8 by treatment with alkaline hydrogen peroxide. Reductive cleavage to the corresponding aldehydes or ketones 9 is efficiently carried out by the action of TiCl3. Addition of methyl magnesium iodide to the methyl ketone derived from 3α- ...