3,5-Diphenyl-2-phosphafuran: Synthesis, Structure, and Thermally Reversible [4 + 2] Cycloaddition Chemistry
3,5-Diphenyl-2-phosphafuran: Synthesis, Structure, and Thermally Reversible [4 + 2] Cycloaddition Chemistry
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3,5-二苯基-2-磷呋喃：合成、结构和热可逆 [4 2] 环加成化学
DOI：
10.1021/acs.joc.0c02025
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发表时间：
2020
期刊：
影响因子：
--
通讯作者：
Cummins, Christopher C.
中科院分区：
文献类型：
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作者：
Riu, Martin-Louis Y.;Cummins, Christopher C.
用二苯并-7-磷杂降冰片二烯EtOPA（A= C14 H10，蒽）（一种乙氧基次膦的来源）处理反式查耳酮，然后进行乙醇的形式消除，以43%的产率产生3，5-二苯基-2-磷杂呋喃（DPF）。结果表明，DPF的磷二烯部分在Diels-Alder反应中是一个有效的二烯，在室温下可与亲二烯体乙炔二甲酸二甲酯（DPF·DMAD，68%）、异戊烯（DPF·异戊烯，73%）和乙烯（DPF·C2 H4，80%）反应。DPF·C2 H4的温和加热导致相应的逆Diels-桤木反应，建立DPF作为能够可逆地结合乙烯的分子。
Treatment oftrans-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·C2H4results in the corresponding retro-Diels–Alder reaction, establishing DPF as a molecule that is able to reversibly bind ethylene.