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Formation of carbon-carbon bonds with radicals derived from the esters of thiohydroxamic acids

✍ Scribed by Derek H.R. Barton; David Crich; Gerhard Kretzschmar

Book ID: 104232545
Publisher: Elsevier Science
Year: 1984
Tongue: French
Weight: 206 KB
Volume: 25
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)80099-x

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✦ Synopsis

Radicals formed from the esters of thiohydroxamic acids readily add to electron deficient olefins to give adducts of potential synthetic value in variable yield. In certain cases the added sulphur function is easily eliminated with reformation of olefin.

Functional group manipulation in complexe natural products can often be carried out advantageously using radical reactions 1. We recently reported that the esters of thiohydroxamic acids readily participate in efficient radical chain sequences generating R-COP* radicals which furnish a good source of R* radicals.2 Thus acids can be decarboxylated to nor-hydrocarbons, nor-halides and nor-hydroperoxides and alcohols in high yield (Scheme).

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