Annulation of the cyclohexane ring by tandem free radical alkylation of a nonactivated delta-carbon atom-intramolecular carbanion cycloalkylation |
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Authors: | Petrovic Cekovic |
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Institution: | Faculty of Chemistry, University of Belgrade, Studentski trg 16, P.O Box 158, 11000 Belgrade, Serbia, Yugoslavia. |
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Abstract: | Annulation of the cyclohexane ring by a combination of free radical and ionic reactions sequences was achieved. Free radical alkylation of the remote nonactivated delta-carbon atom involves addition of delta-carbon radicals, generated by 1,5-hydrogen transfer in alkoxy radical intermediates, to radicophilic olefins, while the polar sequence involves enolate anions as intermediates which undergo a cycloalkylation reaction. Thus, the cyclohexane ring was constructed using diverse acyclic and cyclic structures as precursors of alkoxy radicals. |
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