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A new hypervalent iodine(iii/v) oxidant and its application to the synthesis of 2H-azirines

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Abstract

The reaction of o-nitroiodobenzene and mCPBA in acetic acid was found to afford a novel hypervalent iodine compound, in the structure of which both iodine(III) and iodine(V) moieties coexist. The nitro groups at the ortho phenyl positions were found to be crucial in stabilizing this uncommon structure. This novel hypervalent iodine(III/V) oxidant is proved to be effective in realizing the synthesis of 2-unsubstitued 2H-azirines via intramolecular oxidative azirination, which could not be efficiently achieved by the existing known hypervalent iodine reagents.

Graphical abstract: A new hypervalent iodine(iii/v) oxidant and its application to the synthesis of 2H-azirines

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Article information


Submitted
02 Nov 2019
Accepted
05 Dec 2019
First published
06 Dec 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Advance Article
Article type
Edge Article

A new hypervalent iodine(III/V) oxidant and its application to the synthesis of 2H-azirines

G. Zhang, Y. Wang, J. Xu, J. Sun, F. Sun, Y. Zhang, C. Zhang and Y. Du, Chem. Sci., 2020, Advance Article , DOI: 10.1039/C9SC05536C

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