Die Oxydation von (+)‐(4R)‐4, 8‐Dimethyl‐nonanol‐(1) mit Blei (IV)‐ acetat

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Abstract
The lead tetraacetate oxidation of the optically active aliphatic alcohol 1 in benzene afforded the tetrahydrofurane derivative 3 and the 3‐acetoxy‐tetrahydro‐pyranes 4–6 as major products. The formation of the expected compound 3 in racemic form is interpreted by the stepwise sequence a → b → c → d1–3 → e. The appearance of a carbonium ion of type d3 in the conversion 1 → 3 is in contrast to the direct oxydative ring closure (cf. c → e) which had been postulated previously for cases involving alicyclic educts with sterically fixed reaction centres. The same carbonium ion d3 is considered as a possible intermediate in the formation of compounds 4–6 (cf. f → g → h). The latter process represents a novel type of reaction of monohydric alcohols with lead tetraacetate.