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01242 am a22001693u 4500 |
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141049 |
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|a Riu, Martin-Louis Y
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|a Cummins, Christopher C
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|a 3,5-Diphenyl-2-phosphafuran: Synthesis, Structure, and Thermally Reversible [4 + 2] Cycloaddition Chemistry
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|b American Chemical Society (ACS),
|c 2022-03-07T18:57:15Z.
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|z Get fulltext
|u https://hdl.handle.net/1721.1/141049
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|a © 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.
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|a Article
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|t 10.1021/ACS.JOC.0C02025
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| 773 |
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|t Journal of Organic Chemistry
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