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Applications de la chimie radicalaire des xanthates : Fonctionnalisation de cycles à quatre chaînons. Construction de structures polycycliques.

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.
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https://pastel.archives-ouvertes.fr/pastel-00000994
Contributor : Ecole Polytechnique <>
Submitted on : Tuesday, July 27, 2010 - 9:33:22 AM
Last modification on : Wednesday, January 23, 2019 - 10:29:06 AM
Long-term archiving on: : Thursday, October 28, 2010 - 11:23:08 AM

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  • HAL Id : pastel-00000994, version 1

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Gregori Binot. Applications de la chimie radicalaire des xanthates : Fonctionnalisation de cycles à quatre chaînons. Construction de structures polycycliques.. Chimie de coordination. Ecole Polytechnique X, 2004. Français. ⟨pastel-00000994⟩

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