Factors governing the ratio of isomeric oxabicyclo[3.2.1]octanones formed on Baeyer–Villiger oxidation of some 5-endo,7-anti-disubstituted bicyclo[2.2.1]heptan-2-ones
- 1 January 1978
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 10,p. 1182-1186
- https://doi.org/10.1039/p19780001182
Abstract
It was found that the outcome of Baeyer–Villiger oxidation of 5-endo,7-anti-disubstituted bicyclo[2.2.1]heptan-2-ones was influenced by at least three factors: (i) the electronegativity of the substituent at C-7; (ii) the hydrogen-bonding capability of the substituent at C-5; and (iii) the peracid employed. The optimum substituents and reaction conditions for oxidation of a bicycloheptanone to the corresponding 2-oxabicyclo[3.2.1]octan-3-one were delineated and used in the synthesis of a prostaglandin intermediate.Keywords
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