Comparisons of the diazomethane and Tiffeneau–Demjanov ring expansion reactions on 17β-hydroxy-5α-androstan-3-one and its derivatives have indicated equatorial approach of diazomethane to the C-3 carbonyl and have confirmed that for the corresponding addition of cyanide ion under equilibrating conditions the axial cyano-epimer expected to be favoured thermodynamically is the predominant product.
J. B. Jones and P. Price, J. Chem. Soc. D, 1969, 1478 DOI: 10.1039/C29690001478
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