35599-78-1Relevant articles and documents
A PRACTICAL ALTERNATIVE TO THE HUNSDIECKER REACTION
Barton, Derek H.R.,Crich, David,Motherwell, William B.
, p. 4979 - 4982 (1983)
Carboxylic acid esters derived from N-hydroxy-pyridine-2-thione react with carbon tetrachloride, bromotrichloromethane or iodoform in a radical chain reaction to give the corresponding noralkyl chlorides, bromides or iodides in high yield.
LIGHT INDUCED HALOGENATIVE DECARBOXYLATION OF THIOHYDROXAMIC ESTERS
Dauben, William G.,Kowalczyk, Bruce A.,Bridon, Dominique P.
, p. 2461 - 2464 (2007/10/02)
The generality of lidht initiated halogenative decarboxylation of thiohydroxamic esters was studied.This method gave high yields of alkyl chlorides, bromides and iodides derived from primary, secondary and tertiairy substituted carboxylic acids.
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.