D. Barton, D. Crich, W. Motherwell
1985
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422
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Journal
Tetrahedron
Abstract
Abstract The aliphatic and alicyclic esters of N-hydroxypyridine-2-thione are readily reduced by tributylstannane in a radical chain reaction to furnish nor-alkanes.1 In the absence of the stannane a smooth decarboxylatlive rearrangement occurs to give 2-substituted thiopyridines.1 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.1Similarly these carbon radicals can be captured by halogen atom transfer to give noralkyl chlorides, bromides and iodides. 2 With oxygen in the presence of t-butylthiol the corresponding noralkyl hydroperoxides are formed in another radical chain reaction.3