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Phospholones from Diacetylenic Ketones: Synthesis, Properties, and Reactivity
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström.ORCID iD: 0000-0002-9450-2532
2019 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 84, no 6, p. 3491-3499Article in journal (Refereed) Published
Abstract [en]

The reactivity of phosphanyl phosphonates toward diacetylenic ketones was studied. Reactions resulted in the selective formation of phospholones via phosphaalkene intermediates. Phospholones were obtained in yields of 37-96% depending on the substituent on the acetylenic unit. Reduction of the phenyl-substituted phospholone resulted in the formation of a persubstituted phosphole bearing a hydroxyl group in position 3 in 64% yield, and its oxidation led to oxaphospholone in 77% yield. Both of these modifications led to substantial changes in the optoelectronic properties of the compounds and bathochromic shifts of the longest wavelength absorption maximum.

Place, publisher, year, edition, pages
2019. Vol. 84, no 6, p. 3491-3499
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Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-381078DOI: 10.1021/acs.joc.9b00076ISI: 000461844000039PubMedID: 30788966OAI: oai:DiVA.org:uu-381078DiVA, id: diva2:1306357
Available from: 2019-04-23 Created: 2019-04-23 Last updated: 2019-04-23Bibliographically approved

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Arkhypchuk, Anna I.

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