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Nouvelles applications de la chimie radicalaire des xanthates : Synthèse de molécules organofluorées, de cyanodiènes et δ-lactones insaturées, et d'hétérocycles variés.

Abstract : The radical chemistry has enjoyed two decades a growing success and its applications in organic synthesis have become frequent. The Barton deoxygenation and reduction of halogenated by hydride tributyltin paved the way for a whole class of selective modification reactions functional groups. In recent years, research conducted in the laboratory are focused on Possible applications of radical chemistry in reactions intermolecular, particularly through radical chemistry of xanthates. These compounds indeed provide interesting results in the case of reactions intermolecular addition between carbon radicals and olefins characters varied. It is within this framework is the work presented in this manuscript. The objective of these studies was to develop a series of reactions applicable in synthesis organic. All these reactions are characteristic of using xanthates as a source radicals. The organization of the manuscript is made as follows: In the first part, we present the radical chemistry of xanthates developed at the laboratory. After a brief introduction to radical chemistry, we will focus on the specific function of xanthate, the possible syntheses of this type compounds, and achievements using this method. My work done under the direction of Professor Samir Zard, in collaboration with Jean-Marc Paris and François Metz of Rhodia, are focused on the study of new radicals generated by xanthates, each study with many different applications. The presentation of our work will focus primarily on the study of xanthate trifluoromethylated. We show how they can provide easy access to fluorinated compounds particularly useful, especially in the pharmaceutical industry (Part 2). Subsequently, we will present the formation of new radicals from aldehydes. This method opens a new access to cyanodiènes and δ-unsaturated lactones, and offers innovative solutions for organic synthesis (Part 3). Finally, we will report our work on the radicals formed from salts of aryldiazonium. We show that it is possible to make additions reactions intramolecular radical, allowing access to various heterocycles (Part 4).
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Submitted on : Thursday, July 29, 2010 - 4:32:50 PM
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Lucie Tournier. Nouvelles applications de la chimie radicalaire des xanthates : Synthèse de molécules organofluorées, de cyanodiènes et δ-lactones insaturées, et d'hétérocycles variés.. Chimie organique. Ecole Polytechnique X, 2005. Français. ⟨pastel-00001910⟩

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