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Regioselectivity of the reaction of 3-keto steroids with potassium superoxide

AuthorsÁlvarez, Carlos Enrique ; Francisco, Cosme G. ; Freire, Raimundo ; Hernández, Rosendo ; Salazar, José A.; Suárez, Ernesto ; Betancor, Carmen
Issue Date1986
PublisherRoyal Society of Chemistry (UK)
CitationJournal of the Chemical Society - Perkin Transactions 1986: 1523-1526 (1986)
AbstractThe regioselectivity in the oxidation of different types of 3-keto steroids with potassium superoxide in the presence of 18-crown-6 has been investigated. In all cases, the reaction products are directly related to the enolization process of the substrates. The oxidation of a 2-enolate results in oxidative cleavage of ring A with loss of carbon monoxide to give the lactols (2) and (10) and the aldehyde (8). However, the oxidation of 4-enolates occurs with oxidative cleavage of ring A to give the ketones (7) and (12), the latter with loss of carbon monoxide.
Description4 pages, 2 schemes.
Publisher version (URL)http://dx.doi.org/10.1039/P19860001523
Appears in Collections:(IPNA) Artículos
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