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Theses

CYCLOISOMERISATION D'ALCOOLS ET D'ACIDES CARBOXYLIQUES INSATURES CATALYSEE PAR DES TRIFLATES METALLIQUES. APPLICATIONS EN CHIMIE DES ARÔMES ET PARFUMS.

Abstract : Cyclic ethers and lactones are important compounds in flavor and fragrance chemistry. The scope of this work was focused on the elaboration of a new catalytic system promoting cycloisomerisation of unsaturated alcools and carboxylic acids to cyclic ethers and lactones, respectively.

The use of metallic triflates (Mn+(OTf)n) as Lewis superacids led us to elaborate a new catalytic system involving aluminium or tin triflate (5% molar) in nitromethane.

This system was applied to the synthesis of interesting compounds such as spiroethers, spirodilactones as well as cyclic thioethers and thiolactones. An alternative synthesis of rose oxyde and Doremox® was proposed.

The use of chiral ligands to promote asymetric cyclisations was examined and this study continues in our laboratory.

A theoretical study associated to NMR analysis led to some mechanistic insights with a proposed reaction mechanism.
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https://tel.archives-ouvertes.fr/tel-00205195
Contributor : Lydie Coulombel <>
Submitted on : Wednesday, January 16, 2008 - 12:15:14 PM
Last modification on : Wednesday, October 14, 2020 - 4:24:00 AM
Long-term archiving on: : Tuesday, April 13, 2010 - 6:25:25 PM

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  • HAL Id : tel-00205195, version 1

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Lydie Coulombel. CYCLOISOMERISATION D'ALCOOLS ET D'ACIDES CARBOXYLIQUES INSATURES CATALYSEE PAR DES TRIFLATES METALLIQUES. APPLICATIONS EN CHIMIE DES ARÔMES ET PARFUMS.. Catalyse. Université Nice Sophia Antipolis, 2004. Français. ⟨tel-00205195⟩

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