The olefinic double bond in 17-oxo steroids 1, 5 and 7 is either reduced with diimide very slowly (compound 1) or it cannot be reduced at all (compounds 5 and 7), thus enabling hydrazine (accumulated by disproportionation of the diimide) to react with their respective 17-oxo groups to give hydrazones 3, 6 and 8.
L. Lorenc, L. Bondarenko-Gheorghiu and M. Lj. Mihailovic′, J. Chem. Res. (S), 1998, 102 DOI: 10.1039/A706570A
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