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Issue 40, 2020
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How the combination of PhIO and I2 provides a species responsible for conducting organic reactions through radical mechanisms

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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.

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

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Article information


Submitted
18 Aug 2020
Accepted
24 Sep 2020
First published
24 Sep 2020

Org. Biomol. Chem., 2020,18, 8103-8108
Article type
Paper

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

K. Farshadfar, A. Gouranourimi and A. Ariafard, Org. Biomol. Chem., 2020, 18, 8103
DOI: 10.1039/D0OB01705A

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