138429-93-3Relevant academic research and scientific papers
Investigation into the Reaction between 1α,5α-Epidithio Steroids and Electrophilic Halogenating Reagents: Aspects of the Chemistry of Thiosulphenyl Chlorides and Thiiranium Ions
Barton, Derek H. R.,Hesse, Robert H.,Lindell, Stephen D.,Pechet, Maurice M.
, p. 2845 - 2854 (2007/10/02)
The reaction of sulphuryl dichloride with 1α,5α-epidithioandrostane-3α,17β-diol diacetate afforded a ca. 1:1 mixture of 1α-(chlorodithio) androst-5-ene-3α,17β-diol diacetate and 4β-chloro-1α,5α-epidithioandrostane-3α,17β-diol diacetate.These labile intermediates reacted with various nucleophiles to give a variety of products, many of which represent new or little known classes of thiosteroidal compounds.A number of these appear to arise from an unusual thiiranium ion intermediate.Possible explanations for the differing regioselectivity in the ring opening of the thiiranium ion are advanced.
