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A New Samarium Diiodide Induced Reaction: Intramolecular Attack of Ketyl Radical Anions on Aryl Substituents with Formation of 1,4‐Cyclohexadiene Derivatives
Author(s) -
Dinesh Chimmanamada U.,
Reissig HansUlrich
Publication year - 1999
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19990315)38:6<789::aid-anie789>3.0.co;2-w
Subject(s) - ketyl , aryl , samarium diiodide , intramolecular force , samarium , chemistry , photochemistry , medicinal chemistry , stereochemistry , organic chemistry , benzophenone , alkyl
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=CHCO 2 R, NCH 2 Ph; HMPA=(Me 2 N) 3 PO.