Experimental and theoretical studies of (4 + 1) annulations between α‐oxoketenes and stable phosphorous, nitrogen, or sulfur ylides - Aix-Marseille Université Access content directly
Journal Articles Journal of Physical Organic Chemistry Year : 2019

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

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.
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hal-02059903 , version 1 (07-03-2019)

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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⟩

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