Synthesis, structure, and synthetic potential of arenediazonium trifluoromethanesulfonates as stable and safe diazonium salts

Victor D. Filimonov, Elena A. Krasnokutskaya, Assia Zh Kassanova, Valentina A. Fedorova, Ksenia S. Stankevich, Nikolay G. Naumov, Alexander A. Bondarev, Veronika A. Kataeva

Результат исследований: Материалы для журналаСтатья

2 Цитирования (Scopus)

Выдержка

Aromatic diazonium salts are valuable building blocks for organic synthesis; however, in most cases, they are unstable, unsafe, poorly soluble, and/or expensive. In this paper, we have shown that a variety of stable and safe arenediazonium triflates ArN2 + TfO can be obtained easily and in high yields by diazotization of anilines with tert-butyl nitrite in the presence of trifluoromethanesulfonic acid. Arenediazonium triflates are relatively shelf-stable in the dry state. They dissolve well in water, as well as polar and even nonpolar organic solvents. Less than 800 J/g of energy is released during the thermal decomposition of these salts, which indicates their explosion safety. Arenediazonium triflates have a high reactivity in the known reactions of diazonium chemistry, and undergo an unusual metal-free chlorodediazonization reaction with chloroform and CCl4.

Язык оригиналаАнглийский
Страницы (с-по)665-674
Число страниц10
ЖурналEuropean Journal of Organic Chemistry
Том2019
Номер выпуска4
DOI
СостояниеОпубликовано - 1 янв 2019

Отпечаток

Aniline Compounds
Salts
salts
nitrites
synthesis
Chloroform
aniline
chloroform
shelves
Organic solvents
Explosions
thermal decomposition
explosions
safety
Pyrolysis
reactivity
Metals
chemistry
acids
Water

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Цитировать

Synthesis, structure, and synthetic potential of arenediazonium trifluoromethanesulfonates as stable and safe diazonium salts. / Filimonov, Victor D.; Krasnokutskaya, Elena A.; Kassanova, Assia Zh; Fedorova, Valentina A.; Stankevich, Ksenia S.; Naumov, Nikolay G.; Bondarev, Alexander A.; Kataeva, Veronika A.

В: European Journal of Organic Chemistry, Том 2019, № 4, 01.01.2019, стр. 665-674.

Результат исследований: Материалы для журналаСтатья

Filimonov, Victor D. ; Krasnokutskaya, Elena A. ; Kassanova, Assia Zh ; Fedorova, Valentina A. ; Stankevich, Ksenia S. ; Naumov, Nikolay G. ; Bondarev, Alexander A. ; Kataeva, Veronika A. / Synthesis, structure, and synthetic potential of arenediazonium trifluoromethanesulfonates as stable and safe diazonium salts. В: European Journal of Organic Chemistry. 2019 ; Том 2019, № 4. стр. 665-674.
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AU - Krasnokutskaya, Elena A.

AU - Kassanova, Assia Zh

AU - Fedorova, Valentina A.

AU - Stankevich, Ksenia S.

AU - Naumov, Nikolay G.

AU - Bondarev, Alexander A.

AU - Kataeva, Veronika A.

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N2 - Aromatic diazonium salts are valuable building blocks for organic synthesis; however, in most cases, they are unstable, unsafe, poorly soluble, and/or expensive. In this paper, we have shown that a variety of stable and safe arenediazonium triflates ArN2 + TfO– can be obtained easily and in high yields by diazotization of anilines with tert-butyl nitrite in the presence of trifluoromethanesulfonic acid. Arenediazonium triflates are relatively shelf-stable in the dry state. They dissolve well in water, as well as polar and even nonpolar organic solvents. Less than 800 J/g of energy is released during the thermal decomposition of these salts, which indicates their explosion safety. Arenediazonium triflates have a high reactivity in the known reactions of diazonium chemistry, and undergo an unusual metal-free chlorodediazonization reaction with chloroform and CCl4.

AB - Aromatic diazonium salts are valuable building blocks for organic synthesis; however, in most cases, they are unstable, unsafe, poorly soluble, and/or expensive. In this paper, we have shown that a variety of stable and safe arenediazonium triflates ArN2 + TfO– can be obtained easily and in high yields by diazotization of anilines with tert-butyl nitrite in the presence of trifluoromethanesulfonic acid. Arenediazonium triflates are relatively shelf-stable in the dry state. They dissolve well in water, as well as polar and even nonpolar organic solvents. Less than 800 J/g of energy is released during the thermal decomposition of these salts, which indicates their explosion safety. Arenediazonium triflates have a high reactivity in the known reactions of diazonium chemistry, and undergo an unusual metal-free chlorodediazonization reaction with chloroform and CCl4.

KW - Aromatic substitution

KW - Diazo compounds

KW - Diazonium salts

KW - Solvent effects

KW - Synthetic methods

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