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

Author(s): Pierrot D., Rajzmann Michel, Carissan Yannick, Rodriguez Jean, Bonne Damien, Coquerel Yoann

(Article) Published: Journal Of Physical Organic Chemistry, vol. p.e3939 (2019)

Ref HAL: hal-02059903_v1
DOI: 10.1002/poc.3939
Exporter : BibTex | endNote

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.