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How the combination of PhIO and I2 provides a species responsible for conducting organic reactions through radical mechanisms

Farshadfar, K, Gouranourimi, A and Ariafard, A ORCID: 0000-0003-2383-6380 2020 , 'How the combination of PhIO and I2 provides a species responsible for conducting organic reactions through radical mechanisms' , Organic & Biomolecular Chemistry, vol. 18 , pp. 8103-8108 , doi: 10.1039/d0ob01705a.

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Abstract

A combination of iodosobenzene (PhIO) and molecular iodine (I2) is well-documented to produce a key species capable of conducting various organic reactions through radical mechanisms. This key species is identified here by density functional theory (DFT) calculations to be the hypoiodite radical (IO˙). The calculations show that two equivalents of IO˙ are generated when I2 reacts with two equivalents of PhIO. One of the ensuing IO˙ species acts as a hydrogen abstractor and thus forms an organic radical and the other one is involved in oxidation of the resultant organic radical to afford the final product.

Item Type: Article
Authors/Creators:Farshadfar, K and Gouranourimi, A and Ariafard, A
Keywords: hypervalent compounds, reaction mechanisms, density functional calculations, radical mechanisms
Journal or Publication Title: Organic & Biomolecular Chemistry
Publisher: Royal Soc Chemistry
ISSN: 1477-0520
DOI / ID Number: 10.1039/d0ob01705a
Copyright Information:

Copyright 2020 The Royal Society of Chemistry

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