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Reactions of 1-arylbenziodoxolones with azide anion: Experimental and computational study of substituent effects

Yusubov, Mekhman, Soldatova, Natalia, Postnikov, Pavel, Valiev, Rashid, Svitich, Dmitry, Yusubova, Roza, Yoshimura, Akira, Wirth, Thomas and Zhdankin, Viktor 2018. Reactions of 1-arylbenziodoxolones with azide anion: Experimental and computational study of substituent effects. European Journal of Organic Chemistry 2018 (5) , pp. 640-647. 10.1002/ejoc.201701595

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Abstract

New substituted 1-arylbenziodoxolones were prepared and their reactivity with azide anion nucleophile was investigated. It was found that independent on the presence of substituents, all reactions of 1-arylbenziodoxolones proceed as nucleophilic substitution of the iodonium leaving group in the electron-deficient benziodoxolone benzene ring. The presence of bulky substituents in the ortho-position of the aryl ring slowers the reaction, while the presence of a moderately electron-withdrawing bromine substituent in the para-position to iodine in the benziodoxolone ring moderately increases the rate of substitution. The presence of a strongly electron-withdrawing nitro group in the para-position to iodine in the benziodoxolone ring dramatically increases the rate of substitution. These observations are in agreement with the electronic requirements for internal nucleophilic substitution in the benziodoxole ring. A quantum-chemical computational study of the possible reaction paths is in agreement with the observed effects of substituents on the reactivity of arylbenziodoxolones in this reaction.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: Wiley
ISSN: 1434-193X
Date of First Compliant Deposit: 10 January 2018
Date of Acceptance: 3 January 2018
Last Modified: 27 Jun 2019 11:21
URI: http://orca-mwe.cf.ac.uk/id/eprint/108045

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