Download PDF
Synlett 1996; 1996(6): 587-590
DOI: 10.1055/s-1996-5482
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

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

      >