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Nouvelles applications de la chimie radicalaire des xanthates. -Formulation par voie radicalaire. -Synthèse de spirocétals divers. -Synthèse de composés phosphorés.

Abstract : Radical chemistry has developed an extraordinary way since the beginning of last century. Also, today there are many examples of total synthesis incorporating radical steps leading to the formation of one or even several, carbon-carbon bonds in a particularly soft, most of these applications rely on the use tin hydride. However, the potential of such species is limited by their toxicity and their tendency to reduce premature and often undesirable radical intermediates. The xanthate transfer reaction has no such limitations. This process allows for intermolecular additions of olefin traps little or non-activated and tolerates difficult cyclizations. This makes a very useful tool for training inter-and intramolecular carbon-carbon bonds and provides access to various structures, sophisticated and often highly functionalized in particularly sweet conditions. This is the context of the works presented in this thesis. In Chapter 2 we will see that it is possible to use the chemistry for the radical-formylation of a wide variety of olefins. Chapter 3 describes the synthesis of various spiroacétals implementing the xanthate transfer reaction, while Chapter 4 deals with the radical synthesis of phosphorus compounds. In Chapter 3 it was shown that the radical chemistry of xanthates is a powerful tool that allowed the development of a new effective methodology, providing access to many spirocétals. This approach relies on the functionalization of the xanthate derivative of 1,3-dichloroacetone with the implementation of two-step consecutive intermolecular radical addition followed by spirocyclisation of dihydroxy ketones thus obtained. It is characterized by an extraordinary convergence and flexibility, and complete an interesting ion channels already available.
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Theses
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https://pastel.archives-ouvertes.fr/pastel-00001898
Contributor : Ecole Polytechnique <>
Submitted on : Friday, September 15, 2006 - 8:00:00 AM
Last modification on : Wednesday, January 23, 2019 - 10:29:06 AM
Long-term archiving on: : Saturday, November 26, 2016 - 5:30:14 PM

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Michiel de Greef. Nouvelles applications de la chimie radicalaire des xanthates. -Formulation par voie radicalaire. -Synthèse de spirocétals divers. -Synthèse de composés phosphorés.. Chimie. Ecole Polytechnique X, 2006. Français. ⟨pastel-00001898⟩

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