123084-83-3Relevant academic research and scientific papers
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 (1985)
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.
