Experimental and theoretical studies of (4 + 1) annulations between α‐oxoketenes and stable phosphorous, nitrogen, or sulfur ylides - MédiHAL Accéder directement au contenu
Image (Illustration) Année : 2019

Experimental and theoretical studies of (4 + 1) annulations between α‐oxoketenes and stable phosphorous, nitrogen, or sulfur ylides

Résumé

α‐Oxoketenes generated in situ by a microwave‐assisted Wolff rearrangement at 170°C were found to react with stabilized sulfur ylides in (4 + 1) annulation processes to afford functionalized 3‐hydroxyfurans. Theoretical mechanistic investigations revealed that the reaction proceeds in two steps via a short‐lived betaine intermediate, a general feature of the reactions of α‐oxoketenes with stable phosphorous, nitrogen, and sulfur ylides.

Domaines

Chimie organique

Dates et versions

hal-02362484 , version 1 (13-11-2019)

Licence

Domaine public

Identifiants

  • HAL Id : hal-02362484 , version 1

Citer

David Pierrot, Michel Rajzmann, Yannick Carissan, Jean Rodriguez, Damien Bonne, et al.. Experimental and theoretical studies of (4 + 1) annulations between α‐oxoketenes and stable phosphorous, nitrogen, or sulfur ylides. Illustration. France. 2019. ⟨hal-02362484⟩
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