ChemInform Abstract: QUATERNARY AMMONIUM SALTS WITH PERFLUOROALKYL GROUPS AT THE NITROGEN ATOM

Yagupol’skii, L. M.; Kondratenko, N. V.; Timofeeva, G. N.; Dronkina, M. I.; Yagupolskii, Yurii L.

doi:10.1002/chin.198114156

Cited by 3 publications

(3 citation statements)

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“…Significantly and in contrast with the fluorination by 1 of all the other thiocarbonyl compounds described herein, no difluoride formation was seen. Our method represents an improvement over alternative procedures which utilize toxic and/or corrosive reagents or via N -haloimides in the presence of HF where brominated byproduct formation can be substantial. 13b, …”

Section: Resultsmentioning

confidence: 98%

Fluorination of Thiocarbonyl Compounds with Bis(2-methoxyethyl)aminosulfur Trifluoride (Deoxo-Fluor Reagent): A Facile Synthesis of gem-Difluorides

2000

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Section: Resultsmentioning

confidence: 98%

Fluorination of Thiocarbonyl Compounds with Bis(2-methoxyethyl)aminosulfur Trifluoride (Deoxo-Fluor Reagent): A Facile Synthesis of gem-Difluorides

2000

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“…N-Trifluoromethyl substituted amines can be prepared by chlorine/fluorine exchange with hydrogen fluoride or antimony trifluoride applied to N-(trichloromethyl)amines [158], thiuram disulphides and sulphur tetrafluoride [159,160] or silver fluoride [161], N,N-dialkylformamides and sulphur tetrafluoride in the presence of potassium fluoride [160] and arylisocyanates or phosgene arylimines with hydrogen fluoride (Scheme 53) [162].…”

Section: A-trifluoromethyl Aminesmentioning

confidence: 99%

New trends in the chemistry of α-fluorinated ethers, thioethers, amines and phosphines

Manteau

Pazenok

Vors

et al. 2010

Journal of Fluorine Chemistry

365

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“…Trialkylamines containing the α-difluoromethylene fragment are hydrolytically unstable [3][4][5] as a result of the electron-donating influence of the unshared electron pair of nitrogen. However in the case of nitrogen heterocycles such compounds are significantly more stable, since the nitrogen electron pair is involved in the π−conjugation of the heterocyclic ring.…”

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confidence: 99%

Chemical properties of derivatives of N-difluoromethyl-and N-2-H-tetrafluoroethylpyrazoles

Petko

Sokolenko

Yagupol’skii

2006

Chem Heterocycl Compd

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Nitration, chlorination, bromination, and iodination reactions have been investigated for pyrazole derivatives containing a difluoromethylene fragment directly on a nitrogen atom. Conditions have been found for introducing a cyano group into the nucleus of N-2-H-tetrafluoroethylpyrazole and converting it into carboxyl or tetrazole functions.Pyrazole derivatives enter into the composition of many compounds possessing high biological activity. Several of them, containing fluorinated groupings, are used as medicinal preparations [1] and pesticides [2].Compounds containing a difluoromethylene fragment linked directly with the nitrogen atom have been little studied up to the present. Trialkylamines containing the α-difluoromethylene fragment are hydrolytically unstable [3-5] as a result of the electron-donating influence of the unshared electron pair of nitrogen. However in the case of nitrogen heterocycles such compounds are significantly more stable, since the nitrogen electron pair is involved in the π−conjugation of the heterocyclic ring. Difluoromethyl and 2H-tetrafluoroethyl derivatives of pyrrole [5], imidazole, benzimidazole [6-8], triazole, 3,5-dimethyl-, and 3-carbethoxypyrazole [9, 10] have been synthesized previously.Recently we investigated [11] the chemical properties of N-2-H-tetrafluoroethyl derivatives of pyrrole and imidazole, and found conditions for nitrating, halogenating, and acylating such compounds. As a continuation of investigations in this area we have studied the chemical properties of N-difluoromethyl and N-2H-tetrafluoroethylpyrazoles 1a-d. N N R R (CF 2 ) n H 1a-d a R = H, b R = Me, с R = H, d R = Me; a, b n = 1, c, d n = 2Difluoromethylation of pyrazole, and of 3,5-dimethylpyrazole was carried out in aqueous dioxane medium by the action of chlorodifluoromethane and alkali. N-Difluoromethylpyrazole 1a proved to be an extremely volatile compound. It forms an azeotropically boiling mixture with water and diethyl ether. It is __________________________________________________________________________________________

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ChemInform Abstract: QUATERNARY AMMONIUM SALTS WITH PERFLUOROALKYL GROUPS AT THE NITROGEN ATOM

Cited by 3 publications

References 0 publications

Fluorination of Thiocarbonyl Compounds with Bis(2-methoxyethyl)aminosulfur Trifluoride (Deoxo-Fluor Reagent): A Facile Synthesis of gem-Difluorides

Fluorination of Thiocarbonyl Compounds with Bis(2-methoxyethyl)aminosulfur Trifluoride (Deoxo-Fluor Reagent): A Facile Synthesis of gem-Difluorides

New trends in the chemistry of α-fluorinated ethers, thioethers, amines and phosphines

Chemical properties of derivatives of N-difluoromethyl-and N-2-H-tetrafluoroethylpyrazoles

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