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Synlett 1995; 1995(4): 341-343
DOI: 10.1055/s-1995-4960
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Tricarbonyl Iron Complexes Bearing a Free Diazo Group. I. Synthesis and Cyclocarbonylation Reactions of α-Diazodiene Complexes

Michel Franck-Neumann* , Philippe Geoffroy, Alain Winling
  • *Laboratoire de Chimie Organique Synthétique, Associé au CNRS (URA n°466), Institut de Chimie, Université Louis Pasteur, 1 rue Blaise Pascal, F-67008 STRASBOURG, France
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Publication Date:
31 December 2000 (online)

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The synthesis of α-diazodiene tricarbonyl iron complexes by the Bamford-Stevens reaction was studied. In the case of α-diazoesters, these could be isolated. Their decomposition led to stable (cyclohexa-2,4-dienone) Fe(CO)3 complexes by intramolecular cyclocarbonylation of the formal intermediate carbenes, or directly to phenols, depending on the thermolysis conditions. The structure of the mechanistically important endo-6-methyl-cyclohexadienone complex was determined by X-ray analysis.

Diene - tricarbonyl iron complex - tosylhydrazone - diazoester - cyclohexadienone - phenol - cyclocarbonylation - thermolysis - phase transfer catalysis - copper (acac)2