HYDROXYLATION DE L'ESTRONE ET DE SON ACETATE PAR LE PEROXYDE D'HYDROGENE EN MILIEU SUPERACIDE

Article abstract of DOI:10.1016/S0040-4020(01)91262-1

Estrone 1a and its acetate 1b react with hydrogen peroxide in SbF5-HF to give hydroxylated compounds.The formation of the dienone 2 can be accounted for by reaction of the electrophile H₃O₂⁺ on the neutral substrate, whereas formation of compound 3b implies electrophilic attack on the protonated ester 1b.Higher acidity favours rearrangement of the resulting ion 9 to yield, through a spiro intermediate, the ester 4b.Under the reaction conditions esters 3b and 4b are slowly converted into the corresponding phenols 3a and 4a.