3,5-Diphenyl-2-phosphafuran: Synthesis, Structure, and Thermally Reversible [4 + 2] Cycloaddition Chemistry
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acs.joc.0c02025.pdf
Description
Published version
Size
2.07 MB
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Unknown
Checksum (MD5)
72ad26f338f82233e540e8d55c12f8e1
Author(s)
Riu, Martin-Louis Y.
Cummins, Christopher C
Date Issued
2020
Journal
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
Abstract
© 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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.
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DOI of Published Version
https://doi.org/10.1021/ACS.JOC.0C02025
