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3,5-Diphenyl-2-phosphafuran: Synthesis, Structure, and Thermally Reversible [4 + 2] Cycloaddition Chemistry
| dc.contributor.author | Riu, Martin-Louis Y | |
| dc.contributor.author | Cummins, Christopher C | |
| dc.date.accessioned | 2022-03-07T18:57:15Z | |
| dc.date.available | 2022-03-07T18:57:15Z | |
| dc.date.issued | 2020 | |
| dc.identifier.uri | https://hdl.handle.net/1721.1/141049 | |
| dc.description.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. | en_US |
| dc.language.iso | en | |
| dc.publisher | American Chemical Society (ACS) | en_US |
| dc.relation.isversionof | 10.1021/ACS.JOC.0C02025 | en_US |
| dc.rights | 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. | en_US |
| dc.source | ACS | en_US |
| dc.title | 3,5-Diphenyl-2-phosphafuran: Synthesis, Structure, and Thermally Reversible [4 + 2] Cycloaddition Chemistry | en_US |
| dc.type | Article | en_US |
| dc.identifier.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). | |
| dc.relation.journal | Journal of Organic Chemistry | en_US |
| dc.eprint.version | Final published version | en_US |
| dc.type.uri | http://purl.org/eprint/type/JournalArticle | en_US |
| eprint.status | http://purl.org/eprint/status/PeerReviewed | en_US |
| dc.date.updated | 2022-03-07T18:48:25Z | |
| dspace.orderedauthors | Riu, M-LY; Cummins, CC | en_US |
| dspace.date.submission | 2022-03-07T18:48:27Z | |
| mit.journal.volume | 85 | en_US |
| mit.journal.issue | 22 | en_US |
| mit.license | PUBLISHER_POLICY | |
| mit.metadata.status | Authority Work and Publication Information Needed | en_US |
