Hydrogenolysis of 3α-hydroxycholest-4-ene by aluminium chloride and lithium aluminium deuteride probably proceeds through the formation of an allyl carbonium ion. In the case of 3β-hydroxycholest-4-ene, the results seem to indicate that the reaction does not proceed only through an SN1 mechanism.
M. P. Paradisi and A. Romeo, J. Chem. Soc., Perkin Trans. 1, 1972, 2010 DOI: 10.1039/P19720002010
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