Preparation, X-ray structure, and oxidative reactivity of N-(2-iodylphenyl)tosylamides and 2-iodylphenyl tosylate: Iodylarenes stabilized by ortho-substitution with a sulfonyl group

Artur K. Mailyan, Ivan M. Geraskin, Victor N. Nemykin, Viktor Zhdankin

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Abstract

(Chemical Equation Presented) New tosyl derivatives of 2-iodylaniline and 2-iodylphenol were prepared by the dimethyldioxirane oxidation of the corresponding 2-iodophenyltosylamides or 2-iodophenyl tosylate and isolated as stable, microcrystalline products. Single-crystal X-ray diffraction analysis of N-(2-iodylphenyl)-N,4-dimethylbenzenesulfonamide revealed pseudocyclic structure formed by intramolecular I⋯O interactions between the hypervalent iodine center and the sulfonyl oxygens in the tosyl group. This tosylamide has an excellent solubility in organic solvents and is a potentially useful hypervalent iodine oxidant.

Original languageEnglish (US)
Pages (from-to)8444-8447
Number of pages4
JournalJournal of Organic Chemistry
Volume74
Issue number21
DOIs
StatePublished - Nov 6 2009

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