L. Lorenc et al., REACTIVITY OF SOME UNSATURATED 17-OXO STEROIDS UNDER CONDITIONS OF DIIMIDE REDUCTION, Journal of chemical research. Synopses, (2), 1998, pp. 102-103
The olefinic double bond in 17-oxo steroids 1, 5 and 7 is either reduc
ed with diimide very slowly (compound 1) or it cannot be reduced at al
l (compounds 5 and 7), thus enabling hydrazine (accumulated by disprop
ortionation of the diimide) to react with their respective 17-oxo grou
ps to give hydrazones 3, 6 and 8.