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3,5-Diphenyl-2-phosphafuran: Synthesis, Structure, and Thermally Reversible [4 + 2] Cycloaddition Chemistry

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journal contribution
posted on 07.11.2020, 13:03 by Martin-Louis Y. Riu, Christopher C. Cummins
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.