3,5-Diphenyl-2-phosphafuran: Synthesis, Structure, and Thermally Reversible [4 + 2] Cycloaddition Chemistry
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© 2020 American Chemical Society Treatment of trans-chalcone with dibenzo-7-phosphanorbornadiene EtOPA (A = C14H10, anthracene), a source of ethoxyphosphinidene, followed by formal elimination of ethanol yields 3,5-diphenyl-2-phosphafuran (DPF) in 43% yield. We show that the phosphadiene moiety of DPF is a potent diene in the Diels−Alder reaction and reacts with dienophiles dimethyl acetylenedicarboxylate (DPF·DMAD, 68%), norbornene (DPF·norbornene, 73%), and ethylene (DPF·C2H4, 80%) under ambient conditions. Mild heating of DPF·C2H4 results in the corresponding retro-Diels−Alder reaction, establishing DPF as a molecule that is able to reversibly bind ethylene.
Date issued
2020Department
Massachusetts Institute of Technology. Department of ChemistryJournal
Journal of Organic Chemistry
Publisher
American Chemical Society (ACS)
Citation
Riu, Martin-Louis Y and Cummins, Christopher C. 2020. "3,5-Diphenyl-2-phosphafuran: Synthesis, Structure, and Thermally Reversible [4 + 2] Cycloaddition Chemistry." Journal of Organic Chemistry, 85 (22).
Version: Final published version