Structure and reactivity in steroids
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An analysis was made of a previously proposed mechanism of the oxidation of secondary alcohols by CrO3 in CH3COOH; a formula was derived for the rate of this conversion under equilibrium conditions, and it was shown that the reactivity of the substrates can be characterized by two constants: thermodynamic and kinetic.
The kinetics of the oxidation of the 17β-OH group of derivatives of 3,17β-estradiol, D-3,17αβ-homoestradiol was studied, and it was shown that the experimental data satisfy the equation obtained.
A relationship was established between the reactivity of the 17β- and 17αβ-OH groups of estrogens as a function of the size of the D ring, the coupling of the B and C rings, and the electronic character of the substituent at C3.
KeywordsOxidation Alcohol Experimental Data Steroid Estrogen
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