Abstract The solvolysis of 3β, 19-dihydroxyandrost-5-ene-17-one-3-acetate 19-tosylate (Ib) led to the Δ6-5, 19-cyclo steroid IIa or a variety of 6α-substituted 5, 19-cyclopropanes V depending upon the reaction conditions. The possibility that these reactions proceed through an intermediate homoallylic bridged cation is discussed. The formation of 6β, 19- cyclobutanes from 19-hydroxyandrost-4-ene 3, 17-dione tosylate (VIb) is described
