Oxidation of Testosterone Acetate with Per Acids

Malka Gorodetsky, Naftali Danieli, Yehuda Mazur

Research output: Contribution to journalArticlepeer-review

15 Scopus citations


Oxidation of testosterone acetate (1) with perbenzoic acid and anhydrous perchloric acid produces the enol lactone (2), the epoxy lactones (3), the aldehydo lactones (4), the 5a-formate (5), and the epoxy ketone (6). The product ratio depends on the quantity of per acid used and on the reaction time. Similar oxidation, with aqueous perchloric acid, leads to the lactone (8) and the A-nor ketone (9). Yet another oxidation product, the lactone acid (17), was isolated when m-chloroperbenzoic acid with aqueous perchloric acid was used. The oxidation sequence of testosterone acetate (1), deduced from these results, is discussed.

Original languageEnglish
Pages (from-to)760-764
Number of pages5
JournalJournal of Organic Chemistry
Issue number3
StatePublished - 1 Jan 1967
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry


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