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Superoxide chemistry revisited: Synthesis of tetrachlorosubstituted methylenenortricyclenes
B.M. Budanur,
Published in Beilstein-Institut Zur Forderung der Chemischen Wissenschaften
2014
Volume: 10
   
Pages: 2531 - 2538
Abstract
An unexpected reactivity of the superoxide ion leading to the synthesis of tetrachloroaryl/vinyl-substituted nortricyclenes through its dual mode of action has been reported. KO2 was found to be superior and the only reagent to perform this kind of reaction over other conventional bases. Addition of the antioxidant BHT (2,6-di-tert-butyl-4-methylphenol) improved the yields of methylenenortricyclenes. A complete deuterium incorporation was observed in the superoxide-mediated reaction in DMSO-d6. Friedel-Crafts acylation reactions of 3-methylenenorticyclenes yielded 2-propanone-substituted pentachloronorbornenes. © 2014 Budanur and Khan; licensee Beilstein-Institut. License and terms: see end of document.
About the journal
JournalBeilstein Journal of Organic Chemistry
PublisherBeilstein-Institut Zur Forderung der Chemischen Wissenschaften
ISSN18605397