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- Title
Evaluation of the reactivity and regioselectivity of superelectrophilic iodinating systems.
- Authors
Chaikovskii, V.; Filimonov, V.; Funk, A.
- Abstract
Iodination of o-nitrotoluene in H2SO4 or CF3SO3H at 0°C with compounds having a nitrogen-iodine bond leads to the formation of isomeric mono- and diiodo derivatives whose ratio differs from the statistical value. The reaction of nitrobenzene with 2 equiv of N-I reagents in trifluoromethanesulfonic acid at 0°C takes less than 1 min and yields 79–85% of m-iodonitrobenzene. The electrophilic reactivity of the iodinating agents was estimated by quantum-chemical methods.
- Subjects
REACTIVITY (Chemistry); ELECTROPHILES; NITROTOLUENE; NITROBENZENE; CHEMICAL reactions; NITROGEN isotopes; IODINE compounds; CHEMICAL bonds
- Publication
Russian Journal of Organic Chemistry, 2009, Vol 45, Issue 9, p1349
- ISSN
1070-4280
- Publication type
Article
- DOI
10.1134/S1070428009090073