The photochemical reactions of nitrogen-rich mesoionic 1,3-diphenyltetrazolium heterocycles and related compounds

Araki, Shuki; Hattori, Hiromi; Ogawa, Koji; Kuzuya, Masashi; Inoue, Tomoko; Yamamura, Hisao; Kawai, Maki

doi:10.1039/b009526p

Cited by 11 publications

(3 citation statements)

References 18 publications

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“…112 UV Irradiation of 1,3-diphenyl-5-phenyltetrazolium tetrafluoroborate is accompanied by the evolution of nitrogen and the formation of 1,3-diphenyltetrazolium tetrafluoroborate and benzene. 114 …”

Section: Photolysismentioning

confidence: 99%

1,3- and 1,4-Substituted tetrazolium salts

Войтехович¹,

Гапоник²,

Ивашкевич³

2002

Russ. Chem. Rev.

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The published data on the synthesis, physicochemical The published data on the synthesis, physicochemical properties, structures and reactions of 1,3-(1,3,5)-and 1,4-(1,4,5)-properties, structures and reactions of 1,3-(1,3,5)-and 1,4-(1,4,5)substituted tetrazolium salts are systematised and generalised. substituted tetrazolium salts are systematised and generalised. Their applications as starting compounds in the preparative Their applications as starting compounds in the preparative chemistry of heterocyclic derivatives and some other branches of chemistry of heterocyclic derivatives and some other branches of science and technology are reviewed. The bibliography includes science and technology are reviewed. The bibliography includes 122 references 122 references. .

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Section: Photolysismentioning

confidence: 99%

1,3- and 1,4-Substituted tetrazolium salts

Войтехович¹,

Гапоник²,

Ивашкевич³

2002

Russ. Chem. Rev.

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“…The most interesting and less examined 5-aminotetrazole derivatives are tetrazolium-5-aminides, which can be depicted as 4 by analogy with other mesoionic tetrazoles [11,12]. The first representatives of tetrazole-5-aminides were reported in the 1950s [13,14], whereas next publications were appeared only five decades later, being devoted to the synthesis and photochemistry of 1,3-diaryltetrazolium-5-aminides [15][16][17][18][19][20][21]. NMR studies of a few tetrazole-5-aminides were carried out as a part of studies of mesoionic compounds [22][23][24].…”

Section: Introductionmentioning

confidence: 99%

Mesoionic tetrazolium-5-aminides: Synthesis, molecular and crystal structures, UV–vis spectra, and DFT calculations

Budevich¹,

Войтехович²,

Zuraev³

et al. 2021

Beilstein J. Org. Chem.

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Tetrazolium-5-aminides have been prepared by the tert-butylation of 5-aminotetrazole and its N-methyl derivatives by the t-BuOH/HClO4 system followed by the treatment of the tetrazolium salts by alkali. The mesoionic compounds have been found to show a higher reactivity of the exocyclic N atom in comparison with 5-aminotetrazoles. The compounds reacted with 1,2-dibromoethane and 5-(methylsulfonyl)-1-phenyl-1H-tetrazole with substitution of bromine and methylsulfonyl groups giving the corresponding tetrazolium salts or conjugate aminides. The obtained mesoionic tetrazoles have been characterized by elemental analysis, FTIR, NMR, and UV–vis spectroscopy, TGA/DSC analysis and for 1,3-di-tert-butyltetrazolium-5-aminide, its N,N’-ethylene-bridged bis-derivative and (1,3-di-tert-butyl-1H-tetrazol-3-ium-5-yl)(1-phenyl-1H-tetrazol-5-yl)amide by single crystal X-ray analysis. The structural and spectral features of the tetrazolium-5-aminides are discussed by using quantum-chemical calculations.

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“…The most interesting and less examined 5-aminotetrazole derivatives are tetrazolium-5-aminides, which can be depicted as 4 by analogy with other mesoionic tetrazoles [11,12]. The first representatives of tetrazole-5-aminides were reported in the 1950s [13,14], whereas next publications were appeared only five decades later, being devoted to synthesis and photochemistry of 1,3-diaryltetrazolium-5-aminides [15][16][17][18][19][20][21]. NMR studies of few tetrazole-5-aminides were carried out as a part of studies of mesoionic compounds [22][23][24].…”

mentioning

confidence: 99%

Mesoionic tetrazolium-5-aminides: Synthesis, Molecular and Crystal Structures, UV-Vis Spectra, and DFT Calculations

Budevich¹,

Войтехович²,

Zuraev³

et al. 2020

Preprint

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Tetrazolium-5-aminides have been prepared by tert-butylation of 5-aminotetrazole and its N-methyl derivatives by t-BuOH/HClO4 system followed by treatment of tetrazolium salts by alkali. These mesoionic compounds have been found to show higher reactivity of exocyclic N atom in comparison with 5-aminotetrazoles. They react with 1,2-dibromoethane and 5-(methylsulfonyl)-1-phenyl-1H-tetrazole and substitute bromine and methylsulfonyl groups giving tetrazolium salts or conjugate aminides. Obtained mesoionic tetrazoles have been characterized by elemental analysis, FT-IR, NMR and UV-Vis spectroscopy, TGA/DSC analysis and for 1,3-di-tert-butyltetrazolium-5-aminide, it’s N,N’-ethylene bridged bis-derivative and (1,3-di-tert-butyl-1H-tetrazol-3-ium-5-yl)(1-phenyl-1H-tetrazol-5-yl)amide by single crystal X-ray analysis. Structural and spectral features of tetrazolium-5-aminides are discussed by using quantum-chemical calculations.

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The photochemical reactions of nitrogen-rich mesoionic 1,3-diphenyltetrazolium heterocycles and related compounds

Cited by 11 publications

References 18 publications

1,3- and 1,4-Substituted tetrazolium salts

1,3- and 1,4-Substituted tetrazolium salts

Mesoionic tetrazolium-5-aminides: Synthesis, molecular and crystal structures, UV–vis spectra, and DFT calculations

Mesoionic tetrazolium-5-aminides: Synthesis, Molecular and Crystal Structures, UV-Vis Spectra, and DFT Calculations

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