Issue 0, 1984

Allylic acetoxylation of Δ5-steroids at C-4

Abstract

The allylic acetoxylation of Δ5-steroids at C-4 by reaction with bromine and silver acetate has been shown to depend upon the nature of the C-3 substituent. 2H Labelling studies have shown that the reaction, which proceeds via the 5α,6β-dibromide, involves the trans diaxial elimination of a 4β-proton to form a Δ4-6β-bromide which then undergoes an SN2′ displacement by the incoming acetate assisted by the silver ion.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1984, 2941-2944

Allylic acetoxylation of Δ5-steroids at C-4

J. R. Hanson, P. B. Reese and H. J. Wadsworth, J. Chem. Soc., Perkin Trans. 1, 1984, 2941 DOI: 10.1039/P19840002941

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