Conversion of aliphatic and alicyclic carboxylic acids into nor-hydroperoxides, nor-alcohols, and nor-oxo derivatives using radical chemistry

DHR Barton, D Crich, WB Motherwell

Index: Barton, Derek H. R.; Crich, David; Motherwell, William B. Journal of the Chemical Society, Chemical Communications, 1984 , # 4 p. 242 - 244

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Citation Number: 29

Abstract

We recently reportedl.2 that the esters of N-hydroxypyridine- 2-thione (1) are a very convenient source of carbon radicals. Since the change from a carboxylic acid (R-C02H) to the corresponding nor-alcohol (R-OH) is normally effected in several steps, we have examined an expeditive method for this transformation which exploits this new source of carbon radicals. ... We conceived that carbon radicals would be captured by oxygen in the presence of t-butyl thiol (19), the ...