Evaluation of the reactivity and regioselectivity of superelectrophilic iodinating systems

V. K. Chaikovskii, V. D. Filimonov, A. A. Funk

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Iodination of o-nitrotoluene in H2SO4 or CF 3SO3H 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.

Original languageEnglish
Pages (from-to)1349-1352
Number of pages4
JournalRussian Journal of Organic Chemistry
Volume45
Issue number9
DOIs
Publication statusPublished - Sep 2009

Fingerprint

Regioselectivity
Iodine
Nitrogen
Derivatives
trifluoromethanesulfonic acid
nitrobenzene
2-nitrotoluene

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Evaluation of the reactivity and regioselectivity of superelectrophilic iodinating systems. / Chaikovskii, V. K.; Filimonov, V. D.; Funk, A. A.

In: Russian Journal of Organic Chemistry, Vol. 45, No. 9, 09.2009, p. 1349-1352.

Research output: Contribution to journalArticle

@article{0249e61585a84deeae0cbc2eaf130312,
title = "Evaluation of the reactivity and regioselectivity of superelectrophilic iodinating systems",
abstract = "Iodination of o-nitrotoluene in H2SO4 or CF 3SO3H 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.",
author = "Chaikovskii, {V. K.} and Filimonov, {V. D.} and Funk, {A. A.}",
year = "2009",
month = "9",
doi = "10.1134/S1070428009090073",
language = "English",
volume = "45",
pages = "1349--1352",
journal = "Russian Journal of Organic Chemistry",
issn = "1070-4280",
publisher = "Maik Nauka-Interperiodica Publishing",
number = "9",

}

TY - JOUR

T1 - Evaluation of the reactivity and regioselectivity of superelectrophilic iodinating systems

AU - Chaikovskii, V. K.

AU - Filimonov, V. D.

AU - Funk, A. A.

PY - 2009/9

Y1 - 2009/9

N2 - Iodination of o-nitrotoluene in H2SO4 or CF 3SO3H 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.

AB - Iodination of o-nitrotoluene in H2SO4 or CF 3SO3H 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.

UR - http://www.scopus.com/inward/record.url?scp=70350022790&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=70350022790&partnerID=8YFLogxK

U2 - 10.1134/S1070428009090073

DO - 10.1134/S1070428009090073

M3 - Article

VL - 45

SP - 1349

EP - 1352

JO - Russian Journal of Organic Chemistry

JF - Russian Journal of Organic Chemistry

SN - 1070-4280

IS - 9

ER -