4-Chloromercurioandrosta-4,6-diene-3,17-dione: preparation, X-ray structure determination, and potential utility

Abstract

The novel steroid 4-chloromercurioandrosta-4,6-diene-3,17-dione (2) was obtained as a major side-product during conversions of 6βbromoandrost-4-ene-3,17-dione (1b) into its 6β-fluoro derivative (1a) using HF(pyridine)_n and mercuric oxide. Compound (2) was successfully converted into various 4-substituted steroids (using standard vinyl-mercury methodology), including the disteroidal mercury compound (3c). Crystals of the acetone solvate of (2). 2(HgClC₁₉H₄₀O₂)· acetone, were monoclinic, space group P2₁,Z= 2 with dimensions a= 7.295(8),b= 24.12(1),c= 12.215(12)Å,β= 108.0(1)°. The two independent molecules have equivalent structures with the mercury atoms strongly bound to a chlorine atom and to carbon atom C(4) of the steroid. The acetone molecule forms a weak bridge between the two mercury atoms.