The two-phase oxidation of steroidal 5-en-3 beta-ol (via 5-en-3-ones)
into corresponding 4-en-3,6-diones in diethyl ether with Jones reagent
,vas investigated. It was found that the system Jones reagent/diethyl
ether enables during oxidation, together with molecular mechanics (MM2
), and semiempirical (PM3) calculations, suggest that boat conformatio
n of ring A precedes the formation of corresponding radicals (or catio
ns).