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Royal Society of Chemistry, Chemical Communications, 31(52), p. 5371-5374, 2016

DOI: 10.1039/c6cc00384b

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Why does Togni's reagent I exist in the high-energy hypervalent iodine form? Re-evaluation of benziodoxole based hypervalent iodine reagents

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This paper is available in a repository.

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Abstract

Togni's reagents have become very popular trifluoromethylating reagents in organic synthesis. The existing form of Togni's reagent I is a hypervalent iodine compound which lies much higher in energy than its ether isomer. The high-energy hypervalent iodine form makes Togni's reagent I very effective and versatile. The energy differences between the two forms correlate with the trans influence of the substituents. The five-membered ring in the benziodoxole-based scaffold is an important reason for its existence in the higher-energy form. The relation to Buchwald's 2014 research is discussed.