Why do the Togni reagent and some of its derivatives exist in the high-energy hypervalent iodine form? New insight into the origins of their kinetic stability
Author:
Affiliation:
1. Department of Systems and Mathematical Science
2. Nanzan University
3. Nagoya
4. Japan
5. Department of Chemistry and Applied Biosciences
6. ETH Zürich
7. CH 8093 Zürich
8. Switzerland
Abstract
A scheme for the prediction of the kinetic and thermodynamic stability of Togni-type reagents is presented. The scheme is evaluated based on computations of the isomerization and transition state energies of an array of more than 600 compounds.
Publisher
Royal Society of Chemistry (RSC)
Subject
Physical and Theoretical Chemistry,General Physics and Astronomy
Link
http://pubs.rsc.org/en/content/articlepdf/2017/CP/C7CP05943D
Reference18 articles.
1. V. V. Zhdankin , Hypervalent Chemistry: Preparation, Structure and Synthetic Applications of Polyvalent Iodine Compounds , Wiley , Chichester , 1st edn, 2014
2. Electrophilic Trifluoromethylation by Use of Hypervalent Iodine Reagents
3. Why does Togni's reagent I exist in the high-energy hypervalent iodine form? Re-evaluation of benziodoxole based hypervalent iodine reagents
4. Breaking Down the Reactivity of λ3-Iodanes: The Impact of Structure and Bonding on Competing Reaction Mechanisms
5. Dividing a complex reaction involving a hypervalent iodine reagent into three limiting mechanisms byab initiomolecular dynamics
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2. Bond Strength and Interaction Energies in Togni Reagents: Insights from Molecular Electrostatic Potential-Based Parameters;The Journal of Physical Chemistry A;2024-01-22
3. Cyclic Haloiodanes: Syntheses, Applications and Fundamental Studies;Helvetica Chimica Acta;2021-08-31
4. Relating Bond Strength and Nature to the Thermodynamic Stability of Hypervalent Togni‐Type Iodine Compounds;ChemPlusChem;2021-08
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