Collect. Czech. Chem. Commun. 1999, 64, 1125-1134

Autoxidation vs Hydrolysis in 16α-Acyloxy Steroids

Barbora Slavíková, Alexander Kasal* and Miloš Buděšínský

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic


Some enolizable α-hydroxy ketones are extremely susceptible to oxidation with traces of air in a reaction vessel. Autoxidation can be used in synthesis of oxo acids or diacids and their derivatives. Yet alkaline hydrolysis of the substrate is possible though under strictly air-free conditions.

Keywords: Steroids; Oxidation; Ketones; Mass spectrometry; 1H NMR spectroscopy; Neighbouring group participation.