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Synlett 1996; 1996(6): 587-590
DOI: 10.1055/s-1996-5482
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Transition Metal-Diene Complexes in Organic Synthesis, Part 30.1 On the Mechanism of the Oxidative Cyclizations of Tricarbonyl(η4-cyclohexadiene)iron Complexes: Unequivocal Determination of the Regioselectivity and the Stereospecificity of the Cyclization Process by Deuterium Labeling Studies

Hans-Joachim Knölker* , Frank Budei, Jörn-Bern Pannek, Georg Schlechtingen
  • *Institut für Organische Chemie, Universität Karlsruhe, Richard-Willstätter-Allee, D-76131 Karlsruhe, Germany, Fax: +49(721)698-529; E-mail: knoe@ochhades.chemie.uni-karlsruhe.de
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Publikationsdatum:
31. Dezember 2000 (online)

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Oxidative cyclizations of tricarbonyliron-cyclohexadiene complexes are shown to proceed by stereospecific loss of the 6-syn hydrogen atom. The regioselectivity of these reactions is dependent on the type of the oxidizing reagent. Two-electron oxidants effect a completely regioselective cyclization at C-4 of the cyclohexadiene ligand, while one-electron oxidants provide the product resulting from preferential attack at C-6.

tricarbonyliron complexes - oxidative cyclization - deuterium labeling - stereospecificity - regioselectivity