Binot, Gregori (2004) New applications of xanthate radical chemistry: functionnalisation of 4-membered rings and construction of polycyclic structures. PhD thesis DCSO, EP - DCSO Laboratoire de Synthèse Organique, EP/X p.217.
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Alternative Locations: http://www.imprimerie.polytechnique.fr/Theses/Files/Binot.pdf
Abstract
We have envisioned new applications of the xanthate transfer radical chemistry developed over the past decade in our laboratory.
A first part deals with the use of cyclobutyl radicals generated from xanthates. Numerous ?-branched cyclobutanones could be prepared from intermolecular addition onto various olefins. Associated with a Horner-Emmons-type intramolecular condensation, this reaction provides an access to original cyclobutane-centred polycyclic structures.
A second part reports the synthesis of new xanthates by a Michael-type addition. Radical precursors obtained from conjugate addition of xanthic acid onto ?-enones and ?-enamides could be added either on internal or external olefins for the construction of quaternary centres and polycyclic structures.
Eventually, a novel access to dihydroquinolinones has been designed by coupling this methodology with a radical cyclisation onto an aromatic ring.
| Item Type: | PhD Thesis (PhD) |
|---|---|
| Thesis Supervisor: | Sire, Béatrice |
| Date: | November 2004 |
| Board of examiners: | Renaud, Philippe and Lebreton, Jacques and Salaün, Jacques and Sire, Béatrice and Zard, Samir |
| Ecole Doctorale: | ED 447 ECOLE DOCTORALE DE L'ECOLE POLYTECHNIQUE |
| Discipline: | DCSO |
| Collection (Fonds): | EP/X |
| Institution: | EP/X |
| Department: | EP - DCSO Laboratoire de Synthèse Organique |
| Subjects: | 6. Chemistry, Physical Chemistry and Chemical Engineering |
| Uncontrolled Keywords: | Radicals, Xanthates, Cyclobutanones, Conjugate addition, Cyclisations, Quinolinones, Radicaux carbonés, Xanthates, Cyclobutanones, Addition conjuguée, Cyclisations, Quinoléinones |
Table of content
Chapitre I: Introduction à la chimie radicalaire des xanthates
Chapitre II: Fonctionnalisation de cycles à quatre chaînons par voie radicalaire
Chapitre III: Synthèse de xanthates par addition conjuguée. Applications en chimie radicalaire
Chapitre IV: Nouvelle voie d'accès aux dihydroquinoléinones
Conclusions et perspectives
Partie expérimentale
| ID Code: | 994 |
|---|---|
| Deposited By: | Nadine Garnier |
| Deposited On: | 26 January 2005 |
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