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Reactivity patterns of benzhydryl(mesityl)phosphane oxide: a potential intermediate in carbonyl-carbonyl coupling reactions?
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
2019 (English)In: Phosphorus Sulfur and Silicon and the Related Elements, ISSN 1042-6507, E-ISSN 1563-5325, Vol. 194, no 4-6, p. 575-579Article in journal (Refereed) Published
Abstract [en]

Benzhydryl(mesityl)phosphane oxide 2-H is prepared and its deprotonation and nucleophilicity behavior investigated. Treatment of lithium salts of 2-H with MeI results in methylation at the P-center while the benzyl carbon is not affected. Only upon double lithiation, it is possible to methylate also the benzyl carbon. Di-anion 2-2Li is reactive towards benzaldehyde to afford moderate amounts of triphenylethene after basic work.

Place, publisher, year, edition, pages
2019. Vol. 194, no 4-6, p. 575-579
Keywords [en]
Aldehyde-aldehyde coupling, alkenes, nucleophilicity, reactivity study
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-392062DOI: 10.1080/10426507.2018.1543305ISI: 000473545900091OAI: oai:DiVA.org:uu-392062DiVA, id: diva2:1349812
Conference
22nd International Conference on Phosphorus Chemistry (ICPC), JUL 08-13, 2018, Budapest, HUNGARY
Funder
Swedish Research CouncilAvailable from: 2019-09-10 Created: 2019-09-10 Last updated: 2019-09-10Bibliographically approved

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