Iodohexestrols. I. Synthesis and Photoreactivity of Iodinated Hexestrol Derivatives

The five possible ortho-iodinated hexestrols, containing from 1-4 iodines per molecule, have been synthesized as potential iodine-containing estrogenic ligands. After chromatographic separation and purification, each derivative has been fully characterized by spectroscopic methods. [³H]-3-Iodohexestrol, [¹³¹I]- and [¹²⁵I]-3-iodohexestrol, and [¹²⁵I]-3,5-diiodohexestrol have also been prepared. Photolysis of 3,5-diiodohexestrol in methanol results in rapid deiodination to 3-iodohexestrol; further reduction to hexestrol is slower. Photolysis of 3-iodohexestrol in benzene gives 3-phenylhexestrol.