The extent of deuteriation is reported for the products of the dienone–phenol rearrangement of androsta-1,4-dien-3-ones using as catalysts (i) deuteriated acetic anhydride, acetic acid, and zinc chloride; (ii) deuterium bromide; and (iii) methan [2H]ol, ethyl orthoformate, and [2H2]sulphuric acid. The stereochemistry of the acid-catalysed enolization of 1 -dehydrotestosterone is also reported.
A. G. Avent, J. R. Hanson, L. Yang-Zhi and I. H. Sadler, J. Chem. Soc., Perkin Trans. 1, 1985, 2129 DOI: 10.1039/P19850002129
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