Volume 10, Issue 2 pp. 125-132
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Reactions of cyclotrigermane and germylenes with carbonyl compounds: Cycloadducts and oligomers

Bruno Valentin

Bruno Valentin

Laboratoire “Hétérochimie Fondamentale et Appliquée,” UPRES(A) n°5069, Université Paul Sabatier, 118 Route de Narbonne, 31062 Toulouse Cédex, France

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Annie Castel

Annie Castel

Laboratoire “Hétérochimie Fondamentale et Appliquée,” UPRES(A) n°5069, Université Paul Sabatier, 118 Route de Narbonne, 31062 Toulouse Cédex, France

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Pierre Rivière

Corresponding Author

Pierre Rivière

Laboratoire “Hétérochimie Fondamentale et Appliquée,” UPRES(A) n°5069, Université Paul Sabatier, 118 Route de Narbonne, 31062 Toulouse Cédex, France

Laboratoire “Hétérochimie Fondamentale et Appliquée,” UPRES(A) n°5069, Université Paul Sabatier, 118 Route de Narbonne, 31062 Toulouse Cédex, FranceSearch for more papers by this author
Monique Mauzac

Monique Mauzac

Laboratoire des “Intéractions Moléculaires et Réactivité,” UMR 5623, Université Paul Sabatier, 118 Route de Narbonne, 31062 Toulouse Cédex, France

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Mario Onyszchuk

Mario Onyszchuk

Department of Chemistry, McGill University, 801 Sherbrooke St., West, Montreal, PQ, H3A 2K6, Canada

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A. M. Lebuis

A. M. Lebuis

Department of Chemistry, McGill University, 801 Sherbrooke St., West, Montreal, PQ, H3A 2K6, Canada

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Abstract

Reactions of germylenes, generated by thermolysis of cyclotrigermanes, or of bulky germylenes, with various α-dicarbonyl compounds are described. They proceed through a radical pathway, as confirmed by ESR measurements, to give different types of compounds. In the reaction of (Mes2Ge)3 with fluorenone, formation of the 2:1 ketone/germylene cycloadduct and of the oxadigermetane, resulting from a transient digermene, occurred. In the case of acenaphthene quinone, we observed the first example of cycloaddition between a digermene and an α-diketone. The X-ray crystal structure of the product shows a drastically distorted six-membered ring system. The formation of oligomeric adducts was observed with parabenzoquinone. © 1999 John Wiley & Sons, Inc. Heteroatom Chem 10: 125–132, 1999

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