Thermal rearrangement of 3-oxo-5-vinyl steroids at 350 °C gives bridged steroids with a bicyclo[2.2.1]heptane ring A system; a second, minor product from 5-vinyl-5β-oestrane-3,17-dione (6) has been identified as 5-trans-propenyl-A-nor-5β-oestrane-3,17-dione (9).
F. M. Walliser and P. Yates, J. Chem. Soc., Chem. Commun., 1979, 1025 DOI: 10.1039/C39790001025
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