The reaction of some 1α,2α- and 2α,3α-methylene steroids with hydrobromic acid
Abstract
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.