Issue 4, 1978

Epoxidation of lanost-9(11)-enes. The effect of a β-carbonyl group upon the stereochemistry of epoxidation

Abstract

m-Chloroperbenzoic acid epoxidation of 3β-acetoxylanost-9(11)-en-7-one afforded two isomeric epoxides, the β-isomer being the major product. This result is in contrast with the epoxidation of other 9(11)-olefins having no carbonyl group. It is interpreted in terms of the ‘directive effect’ of the β-carbonyl group which generally influences the steric course of the epoxidation of β-oxo-olefins and is of polar character.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1978, 329-336

Epoxidation of lanost-9(11)-enes. The effect of a β-carbonyl group upon the stereochemistry of epoxidation

Z. Paryzek, J. Chem. Soc., Perkin Trans. 1, 1978, 329 DOI: 10.1039/P19780000329

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