17α-Hydroperoxypregnenes. IV. A Comparative Study of their Fragmentation by Electron Impact and High Temperature Chromatography
- 1 June 1972
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Biochemistry
- Vol. 50 (6) , 706-709
- https://doi.org/10.1139/o72-097
Abstract
The fragmentation of 17α-hydroperoxypregnenolone and 17α-hydroperoxyprogesterone by electron impact and thermolysis is described. It is shown that the fragmentation pattern follows a common pathway for both compounds, determined exclusively by the substituents at ring-D. A new reaction in steroid chemistry, termed deoxygenation, is discovered and its mechanism explained by intramolecular hydrogen abstraction via a six-membered cyclic transition state involving the 20-ketone group.Keywords
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