3,5-Diphenyl-2-phosphafuran: Synthesis, Structure, and Thermally Reversible [4 + 2] Cycloaddition Chemistry
© 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 D...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
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American Chemical Society (ACS)
2022
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| Online Access: | https://hdl.handle.net/1721.1/141049 |
| _version_ | 1811095171395223552 |
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| author | Riu, Martin-Louis Y Cummins, Christopher C |
| author_facet | Riu, Martin-Louis Y Cummins, Christopher C |
| author_sort | Riu, Martin-Louis Y |
| collection | MIT |
| description | © 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. |
| first_indexed | 2024-09-23T16:11:47Z |
| format | Article |
| id | mit-1721.1/141049 |
| institution | Massachusetts Institute of Technology |
| language | English |
| last_indexed | 2024-09-23T16:11:47Z |
| publishDate | 2022 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/1410492022-03-08T03:03:38Z 3,5-Diphenyl-2-phosphafuran: Synthesis, Structure, and Thermally Reversible [4 + 2] Cycloaddition Chemistry Riu, Martin-Louis Y Cummins, Christopher C © 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. 2022-03-07T18:57:15Z 2022-03-07T18:57:15Z 2020 2022-03-07T18:48:25Z Article http://purl.org/eprint/type/JournalArticle https://hdl.handle.net/1721.1/141049 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). en 10.1021/ACS.JOC.0C02025 Journal of Organic Chemistry 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. application/pdf American Chemical Society (ACS) ACS |
| spellingShingle | Riu, Martin-Louis Y Cummins, Christopher C 3,5-Diphenyl-2-phosphafuran: Synthesis, Structure, and Thermally Reversible [4 + 2] Cycloaddition Chemistry |
| title | 3,5-Diphenyl-2-phosphafuran: Synthesis, Structure, and Thermally Reversible [4 + 2] Cycloaddition Chemistry |
| title_full | 3,5-Diphenyl-2-phosphafuran: Synthesis, Structure, and Thermally Reversible [4 + 2] Cycloaddition Chemistry |
| title_fullStr | 3,5-Diphenyl-2-phosphafuran: Synthesis, Structure, and Thermally Reversible [4 + 2] Cycloaddition Chemistry |
| title_full_unstemmed | 3,5-Diphenyl-2-phosphafuran: Synthesis, Structure, and Thermally Reversible [4 + 2] Cycloaddition Chemistry |
| title_short | 3,5-Diphenyl-2-phosphafuran: Synthesis, Structure, and Thermally Reversible [4 + 2] Cycloaddition Chemistry |
| title_sort | 3 5 diphenyl 2 phosphafuran synthesis structure and thermally reversible 4 2 cycloaddition chemistry |
| url | https://hdl.handle.net/1721.1/141049 |
| work_keys_str_mv | AT riumartinlouisy 35diphenyl2phosphafuransynthesisstructureandthermallyreversible42cycloadditionchemistry AT cumminschristopherc 35diphenyl2phosphafuransynthesisstructureandthermallyreversible42cycloadditionchemistry |