Electro-organic reactions. Part VII. The cathodic reduction of carvomenthone, menthone, and camphor
- 1 January 1976
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 8,p. 884-888
- https://doi.org/10.1039/p29760000884
Abstract
The results of cathodic reduction in ethanol of some hindered cyclic ketones (carvomenthone, menthone, and camphor) have been compared with those obtained for unhindered cyclic ketones. Carvomenthone behaves similarly to the unhindered ketones giving predominantly 2e reduction to the alcohol. Menthone gives predominantly 4e reduction to menthane, and camphor can only be reduced [to borneol (84%) and isoborneol (16%)]via the cathodic generation in hexamethylphosphoramide of solvated electrons. The differing results from carvomenthone and menthone are rationalised in terms of a common reaction pathway analogous to that previously proposed for Clemmensen reduction.Keywords
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