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

David Pierrot (1) , Michel Rajzmann (2) , Yannick Carissan (2) , Jean Rodriguez (2) , Damien Bonne (2) , Yoann Coquerel (3, 2)

1 ERIC - Entrepôts, Représentation et Ingénierie des Connaissances
2 ISM2 - Institut des Sciences Moléculaires de Marseille
3 STeRéO

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.

Keywords: annulation; betaines; density functional calculations; synthetic methods; ylides

Domains: Chemical Sciences; Theoretical and/or physical chemistry

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, 2019, pp.e3939. ⟨10.1002/poc.3939⟩. ⟨hal-02059903⟩