ECM - École Centrale de Marseille : UMR7313 (Pôle de l'étoile - Technopole de Château-Gombert - 38 rue Frédéric Joliot-Curie - 13013 Marseille - France)
ECM - École Centrale de Marseille : UMR7313 (Pôle de l'étoile - Technopole de Château-Gombert - 38 rue Frédéric Joliot-Curie - 13013 Marseille - France)
Abstract : 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 processesto 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.
https://hal-amu.archives-ouvertes.fr/hal-02059903 Contributor : Yannick CarissanConnect in order to contact the contributor Submitted on : Thursday, March 7, 2019 - 9:29:21 AM Last modification on : Sunday, June 26, 2022 - 2:37:02 AM Long-term archiving on: : Monday, June 10, 2019 - 4:29:07 PM
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. Journal of Physical Organic Chemistry, Wiley, 2019, pp.e3939. ⟨10.1002/poc.3939⟩. ⟨hal-02059903⟩