Treatment of 17β-acetoxy-1α,2α-methyleneandrost-4-en-3-one under the conditions of the dienone–phenol rearrangement affords 17β-acetoxy-1α-bromomethylandrost-4-en-3-one rather than a phenol. The corresponding 3α-alcohol gave a 1α-bromomethyl-3,5-diene rather than an aromatic compound. 2α,3α-Methyleneandrost-5-ene-4,17-dione also gave a 2α-bromomethylandrost-5-ene-4,17-dione rather than a phenol.
J. R. Hanson and S. G. Knights, J. Chem. Soc., Perkin Trans. 1, 1981, 24 DOI: 10.1039/P19810000024
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