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.
|Number of pages||5|
|Journal||Journal of Organic Chemistry|
|State||Published - 1 Jan 1967|
ASJC Scopus subject areas
- Organic Chemistry