91534-05-3Relevant articles and documents
Decarboxylative radical addition to vinylsulphones and vinylphosphonium bromide: Some further novel transformations of geminal (pyridine-2-thiyl) phenylsulphones
Barton,Boivin,Crepon nee da Silva,Sarma,Togo,Zard
, p. 7091 - 7108 (2007/10/02)
Irradiation of O-acyl derivatives 1 of N-hydroxy-2-thiopyridone with visible light in the presence of phenyl vinyl sulphone or vinyl triphenylphosphonium bromide leads to the corresponding adducts 8 and 9 which can undergo a wide variety of further transformations.
THE INVENTION OF NEW RADICAL CHAIN REACTIONS. PART XIII. HIGH YIELDING DECARBOXYLATIVE CHALCOGENATION OF ALIPHATIC AND ALICYCLIC ACIDS
Barton, Derek H.R.,Bridon, Dominique,Zard, Samir Z.
, p. 449 - 462 (2007/10/02)
Irradiation with a tungsten lamp of mixed anhydrides (e.g. 8) derived from aliphatic or alicyclic carboxylic acids and N-hydroxy-2-pyridine thione 3 in the presence of a disulphide, diselenide or ditelluride gives the corresponding chalcogenide (e.g. 9, 10, or 11) in high yield.The process involves a radical decarboxylation followed by SH2 reaction of the intermediate carbon radical on the dichalcogenide.
THE INVENTION OF RADICAL CHAIN REACTIONS. PART XIV. A DECARBOXILATIVE RADICAL ADDITION TO QUINONES
Barton, Derek H. R.,Bridon, Dominique,Zard, Samir Z.
, p. 5307 - 5314 (2007/10/02)
Irradiation of esters 3 derived from aliphatic or alicyclic carboxylic acids and N-hydroxy-2-thiopyridone in the presence of various quinones gives high yields of the corresponding adducts (e.g. 9) with net loss of carbon dioxide.
THE INVENTION OF NEW RADICAL CHAIN REACTIONS. PART VIII. RADICAL CHEMISTRY OF THIOHYDROXAMIC ESTERS; A NEW METHOD FOR THE GENERATION OF CARBON RADICALS FROM CARBOXYLIC ACIDS.
Barton, Derek H. R.,Crich, David,Motherwell, William B.
, p. 3901 - 3924 (2007/10/02)
The aliphatic and alicyclic esters of N-hydroxy-pyridine-2-thione are readily reduced by tributylstannane in a radical chain reaction to furnish nor-alkanes.In the absence of the stannane a smooth decarboxylative rearrangement occurs to give 2-substituted thiopyridines.The radicals present in this reaction provoke with t-butylthiol an efficient radical reaction with formation of nor-alkane and 2-pyridyl-t-butyl disulphide.Similarly these carbon radicals can be captured by halogen atom transfer to give noralkyl chlorides, bromides and iodides.With oxygen in the presence of t-butylthiol the corresponding noralkyl hydroperoxides are formed in another radical chain reaction.
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.
Conversion of Aliphatic and Alicyclic Carboxylic Acids into nor-Hydroperoxides, nor-Alcohols, and nor-Oxo Derivatives using Radical Chemistry
Barton, Derek H. R.,Crich, David,Motherwell, William B.
, p. 242 - 244 (2007/10/02)
Radicals generated from esters of N-hydroxypyridine-2-thione react smoothly with oxygen in the presence of t-butyl thiol to furnish nor-hydroperoxides, from which the corresponding alcohols and carbonyl derivatives can be readily obtained.
