Diquinanes, Eight-membered Carbocycles and new Di-bridged Bis-π-allyl Complexes by Intramolecular Reactions of Unsaturated Tricarbonyl [Trimethylenemethane] iron Complexes. Non Destructive Ozonolysis of Trimethylenemethane Complexes.

Michel Franck-Neumann; André Kastler

doi:10.1055/s-1995-4853

Synlett 1995; 1995(1): 61-63
DOI: 10.1055/s-1995-4853

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Diquinanes, Eight-membered Carbocycles and new Di-bridged Bis-π-allyl Complexes by Intramolecular Reactions of Unsaturated Tricarbonyl [Trimethylenemethane] iron Complexes. Non Destructive Ozonolysis of Trimethylenemethane Complexes.

Michel Franck-Neumann^* , André Kastler

^*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

Abstract

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Tricarbonyl [TMM] iron complexes bearing an olefinic side chain were oxidized by Me₃NO in boiling benzene. When the TMM and the reactive C=C bond are separated by 3C-spacers, novel di-bridged dicarbonyl [bis-π-allyl] iron complexes, as well as methylenediquinanes or 5-vinylcyclooctenones were obtained selectively, depending on the substitution pattern and the configuration of the starting TMM complexes. Their synthesis was achieved via cross conjugated tricarbonyl [pentadienyl] iron cations and by use of the unprecedented ozonolysis of mixtures of TMM and diene complexes with homoallylic side chains to [TMM] Fe(CO)₃ aldehydes, which resulted in a chemical purification by selective destruction of the diene complexes.

Trimethylenemethane - iron tricarbonyl complexes - decomplexation - bis-π-allyl iron dicarbonyl complexes - diquinanes - cyclooctenones - ozonolysis

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