95717-16-1Relevant articles and documents
HYDROXYLATION DE L'ESTRONE ET DE SON ACETATE PAR LE PEROXYDE D'HYDROGENE EN MILIEU SUPERACIDE
Berrier, C.,Jacquesy, J. C.,Jouannetaud, M. P.
, p. 5135 - 5142 (1984)
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.
