Abstract
The reaction of toluene-p-sulphonyl chloride in pyridine with 5α-cholest-1-en-3β-ol (I; R = C8H17) has been reported to yield directly 1α,5-cyclo-5α-cholest-2-ene (II). This rearrangement is now shown to be initiated by a C-5α to C-3α transannular migration of hydrogen, followed by movement of the π-electrons of the Δ1-bond to give a 1α,5α-bridge. The reaction is then completed by proton extrusion from C-3 to give the cyclosteroid (II). This mechanism has been verified by considering the solvolysis products of 5α-deuteriocholest-1-en-3β-ol and 5α-fluorocholest-1-en-3β-ol.
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