Issue 10, 1990

1:3-Rearrangement of steroidal allylic acetoxy groups during epoxidation

Abstract

Epoxidation of both 4β-acetoxyandrost-5-en-17-one and 6β-acetoxyandrost-4-en-17-one by m-chloroperbenzoic acid affords a similar mixture of 4β-acetoxy-5α,6α-epoxy- and 6β-acetoxy-4α,5α-epoxyandrostan-17-one. This is interpreted in terms of a symmetrical ‘acetoxylinium’(1,3-dioxan-2-ylium) ion and a degree of charge separation in the transition state for epoxidation.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1990, 2667-2669

1:3-Rearrangement of steroidal allylic acetoxy groups during epoxidation

N. Flaih and J. R. Hanson, J. Chem. Soc., Perkin Trans. 1, 1990, 2667 DOI: 10.1039/P19900002667

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