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Synthesis 1995; 1995(5): 587-591
DOI: 10.1055/s-1995-3940
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2-Substituted Bicyclo[3.2.1]oct-2-en-8-ones by Carbonylation of Cycloheptadiene-Derived Iron Carbonyl Complexes Bearing Alkyl-Allyl Subunits

Andreas Hirschfelder, Peter Eilbracht*
  • *Organische Chemie I (FB 3), Universität Dortmund, Otto-Hahn-Str. 6, D-44221 Dortmund, Germany, Fax +49(231)7555363
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Publication Date:
31 December 2000 (online)

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Iron carbonyl complexes 7, generated by the reaction of cationic cycloheptadienyl complex 6 [L = P(OPh)3] with appropriate nucleophiles, can be converted into bicyclooctenones 9 and 10 via carbonylative decomplexation. Treatment of 7 with CO (200 bar) at elevated temperatures yields the ketones 10 as the main products. Thus, carbonylation is accompanied by double bond migration.

bicyclo[3.2.1]oct-2-en-8-one synthesis - carbonylation - iron carbonyl complexes - cationic cycloheptadienyl complexes - nucleophilic addition