American Chemical Society
ja3c11263_si_002.pdf (3.83 MB)

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

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journal contribution
posted on 2023-11-27, 12:06 authored by Tiansi Xin, Christopher C. Cummins
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, RPA (A = C14H10, 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.