Stereochemical studies of monoterpene compounds. Part XI. Rearrangement of 2α-hydroxypinan-3-one in the presence of anhydrous oxalic acid
- 1 January 1972
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 258-260
- https://doi.org/10.1039/p19720000258
Abstract
Treatment of (+)-2α-hydroxypinan-3-one (1) with anhydrous oxalic acid led to the formation of eucarvone (2), carvacrol (3), (+)-dihydro-β-campholenolactone (1,8,8-trimethyl-2-oxabicyclo[3,3,0]octan-3-one)(4), (–)-1,2-campholide (1,8,8-trimethyl-2-oxabicyclo[3,2,1]octan-3-one)(5), (±)-carvone (6), and (+)-α-campholenic acid (7). Conversion of (+)-2α-hydroxypinan-3-one (1) into the ketone (2) and the lactones (4) and (5) is a novel acid-catalysed rearrangement of the pinane skeleton. The mechanistic implications of the rearrangement are discussed.Keywords
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