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Synthesis of Phosphet-2-one Derivatives via Phosphinidene Transfer to Cyclopropenones. | LitMetric

Synthesis of Phosphet-2-one Derivatives via Phosphinidene Transfer to Cyclopropenones.

J Am Chem Soc

Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.

Published: December 2023

AI Article Synopsis

  • The first successful synthesis and structural analysis of free phosphet-2-ones, which are four-membered phosphacyclic compounds, was reported.
  • These compounds were created by transferring phosphinidene from certain phosphorous-containing compounds to cyclopropenones, achieving yields of up to 89%.
  • The study suggests that the production of phosphet-2-ones involves intermediary compounds and further reactions also led to the creation of other related compounds, including some furanone derivatives through a specific catalytic process.

Article Abstract

We report the first synthesis and structural characterization of free, uncomplexed phosphet-2-ones. These unsaturated four-membered phosphacycles were prepared by phosphinidene transfer from dibenzo-7-phosphanorbornadiene compounds, RP ( = CH, anthracene), to cyclopropenones in yields of up to 89%. Theoretical studies suggest that the reaction proceeds through ketene-ylide and ketene-phosphaalkene intermediates. Further transformations of the phosphet-2-ones led to the isolation of more phosphet-2-ones and 1,2-dihydrophosphetes, including two furanone derivatives which are postulated to be produced by intramolecular phosphine-catalyzed [3 + 2] annulations.

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Source
http://dx.doi.org/10.1021/jacs.3c11263DOI Listing

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