Reactivity of alkali and alkaline earth metal tetrafluorobromates towards aromatic compounds and pyridine

Vasily I. Sobolev, Victor D. Filimonov, Roman V. Ostvald, Vyacheslav B. Radchenko, Ivan I. Zherin

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The bromination activity of tetrafluorobromates of alkali and alkali-earth metals increases in the order KBrF4, CsBrF4, RbBrF4 and Ba(BrF4)2. The most active tetrafluorobromate—Ba(BrF4)2 is able to selectively brominate the deactivated aromatic compounds nitrobenzene and 4-nitrotoluene, but not the activated compounds benzene and toluene. In all cases bromination of methyl groups of methylbenzenes does not occur. Ba(BrF4)2 forms the known complex C6H5N·BrF3 when reacted with pyridine. Due to dilution by inert BaF2, this pyridine-based complex is air stable and can be considered as safer and more convenient reagent in comparison with the original fluorobromates; it can selectively brominate benzene and toluene in contrast with tetrafluorobromates.

Original languageEnglish
Pages (from-to)120-123
Number of pages4
JournalJournal of Fluorine Chemistry
Volume192
DOIs
Publication statusPublished - 1 Dec 2016

Fingerprint

Alkaline Earth Metals
bromination
alkaline earth metal
alkaline earth metals
aromatic compounds
Aromatic compounds
Halogenation
Toluene
Alkalies
Benzene
toluene
benzene
alkalies
pyridines
reactivity
Alkali Metals
nitrobenzenes
Dilution
reagents
dilution

Keywords

  • Arenes
  • Bromination
  • Bromine trifluoride
  • Fluorine
  • Tetrafluorobromates

ASJC Scopus subject areas

  • Environmental Chemistry
  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Reactivity of alkali and alkaline earth metal tetrafluorobromates towards aromatic compounds and pyridine. / Sobolev, Vasily I.; Filimonov, Victor D.; Ostvald, Roman V.; Radchenko, Vyacheslav B.; Zherin, Ivan I.

In: Journal of Fluorine Chemistry, Vol. 192, 01.12.2016, p. 120-123.

Research output: Contribution to journalArticle

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AU - Sobolev, Vasily I.

AU - Filimonov, Victor D.

AU - Ostvald, Roman V.

AU - Radchenko, Vyacheslav B.

AU - Zherin, Ivan I.

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N2 - The bromination activity of tetrafluorobromates of alkali and alkali-earth metals increases in the order KBrF4, CsBrF4, RbBrF4 and Ba(BrF4)2. The most active tetrafluorobromate—Ba(BrF4)2 is able to selectively brominate the deactivated aromatic compounds nitrobenzene and 4-nitrotoluene, but not the activated compounds benzene and toluene. In all cases bromination of methyl groups of methylbenzenes does not occur. Ba(BrF4)2 forms the known complex C6H5N·BrF3 when reacted with pyridine. Due to dilution by inert BaF2, this pyridine-based complex is air stable and can be considered as safer and more convenient reagent in comparison with the original fluorobromates; it can selectively brominate benzene and toluene in contrast with tetrafluorobromates.

AB - The bromination activity of tetrafluorobromates of alkali and alkali-earth metals increases in the order KBrF4, CsBrF4, RbBrF4 and Ba(BrF4)2. The most active tetrafluorobromate—Ba(BrF4)2 is able to selectively brominate the deactivated aromatic compounds nitrobenzene and 4-nitrotoluene, but not the activated compounds benzene and toluene. In all cases bromination of methyl groups of methylbenzenes does not occur. Ba(BrF4)2 forms the known complex C6H5N·BrF3 when reacted with pyridine. Due to dilution by inert BaF2, this pyridine-based complex is air stable and can be considered as safer and more convenient reagent in comparison with the original fluorobromates; it can selectively brominate benzene and toluene in contrast with tetrafluorobromates.

KW - Arenes

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KW - Bromine trifluoride

KW - Fluorine

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