A.M. Starosotnikov

N.D. Zelinsky Institute of Organic Chemistry

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Maxim A. Bastrakov

N.D. Zelinsky Institute of Organic Chemistry

ВВ

Вадим В. Качала

N.D. Zelinsky Institute of Organic Chemistry

S. A. Shevelev

N.D. Zelinsky Institute of Organic Chemistry

ИГ

И.В. Глухов

N.D. Zelinsky Institute of Organic Chemistry

СА

С. А. Шевелев

N.D. Zelinsky Institute of Organic Chemistry

Ivan V. Fedyanin

National Research University Higher School of Economics

A. I. Leonov

University of Akron

Pavel A. Belyakov

N.D. Zelinsky Institute of Organic Chemistry

Sergey Yu. Pechenkin

N.D. Zelinsky Institute of Organic Chemistry

АА

Аlexander А. Korlyukov

A. N. Nesmeyanov Institute of Organoelement Compounds

Cooperative Institutions

Russian Academy of Sciences

N.D. Zelinsky Institute of Organic Chemistry

A. N. Nesmeyanov Institute of Organoelement Compounds

Lomonosov Moscow State University

Institut Lavoisier de Versailles

Centre National de la Recherche Scientifique

NS Kurnakova Institute of General and Inorganic Chemistry

State Research Institute of Organic Chemistry and Technology

Academy of Sciences of the Republic of Bashkortostan

D. Mendeleyev University of Chemical Technology of Russia

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CCDC 752651: Experimental Crystal Structure Determination

The Cambridge Structural Database (2010)

Maxim A. Bastrakov A.M. Starosotnikov И.В. Глухов С. А. Шевелев

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/cct862b

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CCDC 1914802: Experimental Crystal Structure Determination

The Cambridge Structural Database (2020)

A.M. Starosotnikov Maxim A. Bastrakov Вадим В. Качала Ivan V. Fedyanin С. А. Шевелев

10.5517/ccdc.csd.cc228htp

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CCDC 752648: Experimental Crystal Structure Determination

The Cambridge Structural Database (2010)

Maxim A. Bastrakov A.M. Starosotnikov Вадим В. Качала И.В. Глухов S. A. Shevelev

10.5517/cct85z6

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CCDC 243974: Experimental Crystal Structure Determination

The Cambridge Structural Database (2004)

Аlexander А. Korlyukov A.M. Starosotnikov Konstantin А. Lyssenko С. А. Шевелев M.Yu. Antipin

10.5517/cc85w4f

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CCDC 1956986: Experimental Crystal Structure Determination

The Cambridge Structural Database (2021)

Maxim A. Bastrakov A.M. Starosotnikov I.V. Fedyanjin Igor L. Dalinger

10.5517/ccdc.csd.cc23pdlt

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CCDC 752650: Experimental Crystal Structure Determination

The Cambridge Structural Database (2010)

Maxim A. Bastrakov A.M. Starosotnikov И.В. Глухов S. A. Shevelev

10.5517/cct8619

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The versatile electrophilic reactivity of 4,6-dinitrobenzo[d]isoxazole-3-carbonitrile

Organic & Biomolecular Chemistry (2009)

Betty Cottyn A.M. Starosotnikov Dominique Vichard Régis Goumont С. А. Шевелев

The interaction of 4,6-dinitrobenzo[d]isoxazole-3-carbonitrile (5a) with methoxide ion has been kinetically investigated in methanol and a 20:80 (v/v) MeOH-Me2SO mixture. In methanol, stopped-flow experiments have revealed that a monomethoxyl σ-adduct (5a-Me) is first formed, resulting from a fast MeO− addition at the unsubstituted 7-carbon. Rate and equilibrium constants for this σ-complexation process could be determined, allowing a ranking of 5a within the pKa scale established for Meisenheimer electrophiles in methanol. With a pKa value of 13.50, the electrophilicity of 5a falls in the range of 1,3,6,8-tetranitronaphthalene, 2,4-dinitrothiophene or 4-nitrobenzofuroxan. This corresponds to a two-pKa units increase in electrophilicity from that of TNB, the common reference in σ-complex chemistry but it is notably below that of so-called superelectrophilic molecules like 4,6-dinitrobenzofuroxan. In addition to its ease of σ-complexation, 5a is found to undergo a slow but thermodynamically favourable addition of MeO− to the cyano group bonded to the isoxazole ring, leading to a complete conversion of the adduct 5a-Me into a dinitroimidate 6. The reactivity of 6 could be kinetically assessed. Going to 80% Me2SO still afforded initially the adduct 5a-Me but this anionic species undergoes addition of a second molecule of MeO− to the CN group, giving a dianion whose structure is unprecedented in the literature. Combining the above results with synthetic observations showing that 5a can readily contribute to SNAr reactions under appropriate experimental conditions emphasizes the multifaceted electrophilic reactivity of this electron-deficient heterocycle.

Isoxazole

Reactivity

Electrophilic substitution

Metalation

10.1039/b820256g

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Citations (11)

CCDC 737503: Experimental Crystal Structure Determination

The Cambridge Structural Database (2012)

Maxim A. Bastrakov A.M. Starosotnikov Sergey Yu. Pechenkin Вадим В. Качала И.В. Глухов

10.5517/ccsrffc

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