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 |
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Authors: | Derek H.R. Barton David Crich William B. Motherwell |
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Affiliation: | Institut de Chimie des Substances Naturelles, C.N.R.S., 91190 Gif-sur-Yvette, France |
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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 -butylthiol an efficient radical reaction with formation of nor-alkane and 2-pyridyl--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 |
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