Unsaturated Sultones from Unsaturated Sulfonates: Synthesis by Ring-Closing Metathesis and Reactivity

Alexandre Le Flohic; Christophe Meyer; Janine Cossy; Jean-Roger Desmurs; Jean-Christophe Galland

doi:10.1055/s-2003-38363

LETTER

Unsaturated Sultones from Unsaturated Sulfonates: Synthesis by Ring-Closing Metathesis and Reactivity

Alexandre Le Flohic^a, Christophe Meyer^a, Janine Cossy*^a, Jean-Roger Desmurs^b, Jean-Christophe Galland^b
^a Laboratoire de Chimie Organique, associé au CNRS, ESPCI, 10 rue Vauquelin, 75231 Paris Cedex 05, France
Fax: +33(0)140794660; e-Mail: janine.cossy@espci.fr;
^b Rhodia, Centre de Recherche de Lyon, 85 rue des Frères Perret, BP 62, 69192 Saint Fons Cedex, France

Abstract

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Abstract

Unsaturated sultones can be efficiently synthesized by ring-closing metathesis of the corresponding unsaturated sulfonates derived from primary and secondary alkenols or alkynols. These compounds can be converted to 1,3-dienes under basic conditions in the presence of carbenoid species.

Key words

sulfonate - cyclization - metathesis - sultone - metalation - carbenoid - diene

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Referenzen

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