Peroxydisulphate Oxidation of Steroidal Olefins

Steroid Research Laboratory, Department of Chemistry, Aligarh Muslim University, Aligarh 202 002 Manuscript received 10 January 1990, revised 24 August 1990, accepted 21 November 1990 Oxidation of some steroidal olefins with K2S2O8. proceeded very smoothly in acetic acid without any catalyst. Cholest-5-ene (1) and its 3β-acetoxy (1a), 3β chloro (1b) analogues provided the corresponding 6-ketones (2, 2b) alongwith some additional products (3-3d). Cholest-3 5-diene (4) afforded the diones (5, 5a) and 6-nitrocholesta-3 5-diene (4a) yielded some new interesting compounds (6, 7- 7c) in which nitrocholest-5-ene moiety remained unaffected. The structures of the products have been established on the basis of their analytical and spectral (ir, 1H nmr, mass) data