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Facile oxidative rearrangements using hypervalent iodine reagents

Singh, Fateh Veer, Rehbein, Julia and Wirth, Thomas ORCID: 2012. Facile oxidative rearrangements using hypervalent iodine reagents. ChemistryOpen 1 (6) , pp. 245-250. 10.1002/open.201200037

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Aromatic substituents migrate in a novel oxidative cyclization mediated by iodine(III) reagents. 4-Arylbut-3-enoic acids are cyclized and rearranged to 4-arylfuran-2(5H)-ones by hypervalent iodine compounds in good to excellent yields under mild reaction conditions. Other ring sizes are also accessible. The mechanism of the reaction is described in detail, and calculations highlight the cationic nature of the intermediates in the rearrangement. The fast access to heavily substituted furanones is used for the synthesis of biologically active derivatives.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Uncontrolled Keywords: calculations; cyclizations; hypervalent iodine; oxidations; rearrangements
Publisher: Wiley-VCH
ISSN: 2191-1363
Last Modified: 24 Oct 2022 10:42

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