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Synthesis 1996; 1996(4): 488-494
DOI: 10.1055/s-1996-4232
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Synthesis of Regio- and Stereoselectively Substituted Bicyclooctenones 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; E-mail eilbrach@citrin.chemie.uni-dortmund.de
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Publication Date:
31 December 2000 (online)

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The addition of appropriate nucleophiles to cationic cycloheptadienyl iron complexes of type 7 leads to alkyl-allyl complexes 8. These compounds can be converted to bicyclic ketones containing a bicyclo[4.1.1]- or a [3.2.1]octenone substructure via oxidative or carbonylative decomplexation. The methods described provide a systematic access to regio- and stereoselectively mono- and disubstituted bicyclooctenones.

iron carbonyl complexes - nucleophilic attack - alkyl-allyl complexes - carbonylation - bicyclooctenones