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.
Document type :
Journal articles
Complete list of metadatas

Cited literature [19 references]  Display  Hide  Download

https://hal-amu.archives-ouvertes.fr/hal-02059903
Contributor : Yannick Carissan <>
Submitted on : Thursday, March 7, 2019 - 9:29:21 AM
Last modification on : Wednesday, April 3, 2019 - 1:11:53 AM
Long-term archiving on : Monday, June 10, 2019 - 4:29:07 PM

File

2019JPOC-asap-(4+1)-oxoketene-...
Publication funded by an institution

Licence


Distributed under a Creative Commons Attribution 4.0 International License

Identifiers

Citation

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⟩

Share

Metrics

Record views

79

Files downloads

5