Singh, Fateh Veer, Rehbein, Julia and Wirth, Thomas ORCID: https://orcid.org/0000-0002-8990-0667 2012. Facile oxidative rearrangements using hypervalent iodine reagents. ChemistryOpen 1 (6) , pp. 245-250. 10.1002/open.201200037 |
Official URL: http://dx.doi.org/10.1002/open.201200037
Abstract
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 |
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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 |
URI: | https://orca.cardiff.ac.uk/id/eprint/45498 |
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