Preparation and X-ray structural study of 1-arylbenziodoxolones

Mekhman S. Yusubov, Roza Y. Yusubova, Victor N. Nemykin, Viktor Vladimirovich Zhdankin

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Abstract

Various 1-arylbenziodoxolones can be conveniently prepared from 2-iodobenzoic acid and arenes by a one-pot procedure using Oxone (2KHSO ₅·KHSO₄·K₂SO₄) as an inexpensive and environmentally safe oxidant. This procedure is also applicable for the synthesis of the 7-methylbenziodoxolone ring system using 2-iodo-3-methylbenzoic acid as starting compound. Structures of four 1-arylbenziodoxolone derivatives were established by single-crystal X-ray diffraction analysis. An enhanced reactivity of 1-aryl-7-methylbenziodoxolones toward nucleophiles compared to unsubstituted 1-arylbenziodoxolones has been found.

Original language	English
Pages (from-to)	3767-3773
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	78
Issue number	8
DOIs	https://doi.org/10.1021/jo400212u
Publication status	Published - 19 Apr 2013

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ASJC Scopus subject areas

Organic Chemistry

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Yusubov, M. S., Yusubova, R. Y., Nemykin, V. N., & Zhdankin, V. V. (2013). Preparation and X-ray structural study of 1-arylbenziodoxolones. Journal of Organic Chemistry, 78(8), 3767-3773. https://doi.org/10.1021/jo400212u

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abstract = "Various 1-arylbenziodoxolones can be conveniently prepared from 2-iodobenzoic acid and arenes by a one-pot procedure using Oxone (2KHSO 5·KHSO4·K2SO4) as an inexpensive and environmentally safe oxidant. This procedure is also applicable for the synthesis of the 7-methylbenziodoxolone ring system using 2-iodo-3-methylbenzoic acid as starting compound. Structures of four 1-arylbenziodoxolone derivatives were established by single-crystal X-ray diffraction analysis. An enhanced reactivity of 1-aryl-7-methylbenziodoxolones toward nucleophiles compared to unsubstituted 1-arylbenziodoxolones has been found.",

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AU - Yusubov, Mekhman S.

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AU - Nemykin, Victor N.

AU - Zhdankin, Viktor Vladimirovich

PY - 2013/4/19

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AB - Various 1-arylbenziodoxolones can be conveniently prepared from 2-iodobenzoic acid and arenes by a one-pot procedure using Oxone (2KHSO 5·KHSO4·K2SO4) as an inexpensive and environmentally safe oxidant. This procedure is also applicable for the synthesis of the 7-methylbenziodoxolone ring system using 2-iodo-3-methylbenzoic acid as starting compound. Structures of four 1-arylbenziodoxolone derivatives were established by single-crystal X-ray diffraction analysis. An enhanced reactivity of 1-aryl-7-methylbenziodoxolones toward nucleophiles compared to unsubstituted 1-arylbenziodoxolones has been found.

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10.1021/jo400212u