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Digitale Medien

Barbier-Type Reactions of Cyclic Acid Anhydrides and Keto Acids Mediated by an SmI2-(NiI2-Catalytic) System - Preparation of Disubstituted Lactones (1998)

Machrouhi, Fouzia ; Pârlea, Elena ; Namy, Jean-Louis

Weinheim : Wiley-Blackwell

Liebigs Annalen 1998 (1998), S. 2431-2436

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Details

ISSN: 1434-193X

Schlagwort(e): Anhydrides ; Barbier reactions ; Lactones ; Nickel diiodide ; Samarium diiodide ; Chemistry ; General Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: Cyclic acid anhydrides (succinic and glutaric anhydrides and some of their derivatives) undergo fast Barbier-type reactions mediated by samarium diiodide in the presence of catalytic amounts of nickel diiodide (1 mol-% with respect to SmI2), to give disubstituted lactones in high yields. Without NiI2 no reaction occurs. Various alkyl and allyl iodides can be used. In these reactions the formation of a samarium keto carboxylate intermediate is likely; as a matter of fact, keto carboxylic acids react under similar conditions to also yield disubstituted lactones. It is demonstrated that lactonisation occurs during hydrolysis of the reaction.

Zusätzliches Material: 3 Tab.

Materialart: Digitale Medien

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