Treatment of 3β-acetoxy-6-nitrocholest-5-ene with an excess of lithium dimethylcuprate gives 3α,5α-cyclocholestan-6-one (E)-oxime; its Beckmann rearrangement product, 3α,5α-cyclo-6-aza-B-homocholestan-7-one, failed to undergo a ‘retro-Beckmann’ rearrangement.
S. Stiver and P. Yates, J. Chem. Soc., Chem. Commun., 1983, 50 DOI: 10.1039/C39830000050
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