The oxidations of the 2-hydroxymethylene derivatives [(II) and (VII)] of 4,4-dimethylcholest-5-en-3-one and lupan-3-one with alkaline hydrogen peroxide to 2,3-seco-diacids are complicated by rearrangements leading to A-nor-2-carboxylic acids. Ring contraction is favoured by the presence of the 5,6-double bond in the former series.
D. J. Hampson, G. D. Meakins and D. J. Morris, J. Chem. Soc. C, 1966, 1277 DOI: 10.1039/J39660001277
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