104543-10-4Relevant academic research and scientific papers
The Invention of New Radical Chain Reactions. Part 9. Further Radical Chemistry of Thiohydroxamic Esters; Formation of Carbon-Carbon Bonds
Barton, Derek H.R.,Crich, David,Kretzschmar, Gerhard
, p. 39 - 54 (2007/10/02)
Carbon radicals derived from the esters of several types of thiohydroxamic acids have been trapped in a number of different ways.Particular attention has been paid to carbon-carbon bond formation by addition to suitably activated ethylenic linkages.Carboxylic acids can be conveniently converted into homo- and bishomo-acids by free radical chemistry based on thiohydroxamic esters.In a coda the tautomerism of the thiohydroxamic acids have been examined by physical methods.It is confirmed that the esters used are derivatives of the thione tautomer.
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-VITAMIN D3 SIDE CHAIN FROM BILE ACIDS.
Barton, Derek H.R.,Togo, Hideo,Zard, Samir Z.
, p. 5507 - 5516 (2007/10/02)
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 methyl ketone derived from 3α-acetoxy 11-oxo cholanic acid gives steroid 10 possessing the 25-hydroxycholesterol side chain of the vitamin D3 metabolites.Radical additions to 1-phenylthio-2-nitropropene 11 have been briefly studied.
FORMATION OF CARBON-CARBON BONDS WITH RADICALS DERIVED FROM THE ESTERS OF THIOHYDROXAMIC ACIDS
Barton, Derek H. R.,Crich, David,Kretzschmar, Gerhard
, p. 1055 - 1058 (2007/10/02)
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.
