3,5-二苯基-2-膦呋喃：合成、结构和热可逆[4+2]环加成化学。
3,5-Diphenyl-2-phosphafuran: Synthesis, Structure, and Thermally Reversible [4 + 2] Cycloaddition Chemistry.
机构信息
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
出版信息
J Org Chem. 2020 Nov 20;85(22):14810-14816. doi: 10.1021/acs.joc.0c02025. Epub 2020 Nov 7.
Treatment of -chalcone with dibenzo-7-phosphanorbornadiene EtOP ( = CH, 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·CH, 80%) under ambient conditions. Mild heating of DPF·CH results in the corresponding retro-Diels-Alder reaction, establishing DPF as a molecule that is able to reversibly bind ethylene.
用二苯并-7-磷杂降蒈烯 EtOP（=CH，蒽）处理 -查尔酮，这是乙氧基磷亚基的来源，然后通过乙醇的正式消除，以 43%的收率得到 3,5-二苯基-2-磷杂呋喃（DPF）。我们表明，DPF 的膦二烯部分是 Diels-Alder 反应中的一种强二烯，并且在环境条件下与亲二烯体二甲基丙二炔酸二甲酯（DPF·DMAD，68%）、降冰片烯（DPF·norbornene，73%）和乙烯（DPF·CH，80%）反应。DPF·CH 的温和加热导致相应的反 Diels-Alder 反应，证明 DPF 是一种能够可逆地结合乙烯的分子。
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