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Synthesis, Characterization and Unusual Reactivity of Vinylbenziodoxolones-Novel Hypervalent Iodine Reagents
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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Number of Authors: 6
2016 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 22, no 45, 16066-16070 p.Article in journal (Refereed) Published
Abstract [en]

A novel type of hypervalent iodine(III) reagents, vinylbenziodoxolones (VBX), has been synthesized in a one-pot reaction from 2-iodobenzoic acid. VBX is bench stable, has been thoroughly characterized and the cyclic structure is supported by X-ray analysis. The reactivity of VBX was investigated in vinylation of nitrocyclohexane, and delivered vinylated products with opposite regioselectivity compared to acyclic vinyl(aryl) iodonium salts. The reagents could become a powerful tool in vinylation reactions under both metal-free and metal-catalyzed conditions.

Place, publisher, year, edition, pages
2016. Vol. 22, no 45, 16066-16070 p.
Keyword [en]
benziodoxolones, hypervalent compounds, structure analysis, synthetic methods, vinylation
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-136921DOI: 10.1002/chem.201603955ISI: 000387132800014PubMedID: 27629653OAI: oai:DiVA.org:su-136921DiVA: diva2:1061677
Available from: 2017-01-03 Created: 2016-12-19 Last updated: 2017-01-03Bibliographically approved

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Stridfeldt, ElinErtan, AnneOlofsson, Berit
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