Preparation and X-ray structural study of 1-arylbenziodoxolones

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

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo400212u

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@article{7e13cb84dec847b2a6e42fa0c3d9444c,

title = "Preparation and X-ray structural study of 1-arylbenziodoxolones",

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.",

author = "Yusubov, {Mekhman S.} and Yusubova, {Roza Y.} and Nemykin, {Victor N.} and Zhdankin, {Viktor Vladimirovich}",

year = "2013",

month = apr,

day = "19",

doi = "10.1021/jo400212u",

language = "English",

volume = "78",

pages = "3767--3773",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "8",

}

TY - JOUR

T1 - Preparation and X-ray structural study of 1-arylbenziodoxolones

AU - Yusubov, Mekhman S.

AU - Yusubova, Roza Y.

AU - Nemykin, Victor N.

AU - Zhdankin, Viktor Vladimirovich

PY - 2013/4/19

Y1 - 2013/4/19

N2 - 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.

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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