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  • Title: A New Samarium Diiodide Induced Reaction: Intramolecular Attack of Ketyl Radical Anions on Aryl Substituents with Formation of 1,4-Cyclohexadiene Derivatives.
    Author: Dinesh CU, Reissig HU.
    Journal: Angew Chem Int Ed Engl; 1999 Mar 15; 38(6):789-791. PubMed ID: 29711804.
    Abstract:
    Beware of samarium diiodide and aryl ketones! If the ketyl radical anion which is formed by electron transfer finds a properly placed aryl group, a highly diastereoselective cyclization may occur. After the transfer of a second electron and protonation bi- and polycyclic products with a common 1,4-cyclohexadiene moiety may be isolated [Eq. (a)]. X=CHCO2 R, NCH2 Ph; HMPA=(Me2 N)3 PO.
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