ORGANOFLUORINE CHEMISTRY

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Department of chemistry of fluoroorganic compounds

Department was created in 1965. Prof., Dr. hab L.M.Yagupolskii was the head of department up to 1988.
Department is engaged in the synthesis and studies of reactivity of fluoro-containing of heteroatomis derivatives of methane, aromatic and heterocyclic compounds, their usage in the synthesis of practically usefull substances.

Research directions

• creating of strong and superstrong electron-withdrawing substituents and  super-acids containing  nitrogen, sulfur and selenium atoms (L.M.Yagupolskii, Yu.L.Yagupolskii, N.V.Kondratenko, R.Yu.Garlyauskaite); ;
• development of synthesis of di- and tri(fluorosulfonyl)methanes, investigation of their properties as CH-acids (Yu.L.Yagupolskii, N.V.Pavlenko, T.I.Savina);
• investigation of properties of conjugated polyfluoromethine systems with terminal aromatic rings, polymethine and cyanine dyes with fluorinated chains (M.M.Kremlev, S.V.Pazenok, L.M.Yagupolskii);
• synthesis and investigation of polyfluorinated phosphoranions, cations and phosphoranes; their potential for anionic fluorination and fluoroalkylation of organic and organoelement compounds. Reactions of nucleophilic substitution at four- and five-coordinated phosphorus bonded with two or three perfluoroalkyl radicals and development of ñonvenient routes of synthesis of phosphine oxides phosphinic- and   phosphonic carboxylic acids (A.A.Kolomeitsev, N.V.Pavlenko Yu.L.Yagupolskii);
• synthesis and study of perfluorinated bismuth and antimony derivatives (Yu.L.Yagupolskii, N.V.Kirij);
• study of dependence fluorine atoms introduction instead of hydrogen ones in terminal substiuents of conjugated aromatic mesogens on their liquid crystalline properties (Yu.A.Fialkov, S.V.Shelyazhenko).

1. L.M.Yagupolskii. Aromatic and heterocyclic compounds with fluoro-containing substituents. - Kyiv: Naukova Dumka, 1988.- 283 p.
2.Organofluorine compounds in medicinal chemistry and biomedical applications / Edt. R. Filler, Y.Kobayashi, L.M.Yagupolskii.
Fluorine-containing cardiovascular drugs. / L.M.Yagupolskii, I.I.Maletina, B.M.Klebanov.  - Elseveier Science Publishers B.V., 1993. - P. 73-99.
3.New fluorinated agents in Organic synthesis / Edt. L.S.German and S.V.Zemskov/, V.V.Bardin and Yu.L.Yagupolskii . Xenon difluoride, p. 63; A.I.Burmakov, B.V.Kunshenko and L.A.Alekseeva. New usage of sulfur tetrafluoride in organic synthesis.- Novisibirsk: Nauka, 1987.- p.197.
4.New fluorinated agents in Organic synthesis / Edt. L.S. German, S.Zemskov.- Berlin: Springer-Verlag.- 1989. - 283 P.
5.L.M.Yagupolskii, A.Ya. Ilchenko. Aromatic compounds with fluorine-containing substituents. /Ed. M.E.Volpin.- Amsterdam: Harwood Academic Publishers Gmbh, 1984.-//Chemistry Rev., Soviet Scientific Reviews, Section B.-Vol.5.-P.347-397.
6.L.M.Yagupolskii, A.Ya. Ilchenko, N.V.Kondratenko. Electronic nature of fluorine-containing substituents. //Uspekhi Khimii.-1974.-Vol. 43.-p. 64-94.
7.L.M.Yagupolskii, A.Ya. Ilchenko, L.Z.Gandelsman. Fluorine-containing dyes.// Uspekhi Khimii.-1983.-Vol. 52.-p. 1732-1759.
8.  L.M.Yagupolskii. Aromatic compounds with new fluorine-containing substituents // J. Fluor. Chem. - 1987. - Vol. 36, N 1.- P. 1-28.
9.E.B.Lifshits, D.Ya. Shagalova, L.M.Yagupolskii. Imidocarbocyanines - spectral sensitizers of photografic silver halide emulsions // Dyes and Pigments. - 1984. - Vol. 5, N 5- P. 377-398.
10.B.M.Krasovitskii, D.G.Pereyaslova, V.T. Skripkina, L.M.Yagupolskii, V.I.Popov. Organic luminofores with fluorine-containing substituents. // Dyes and Pigments.- 1988.- Vol. 9.- P. 21-35.
11.L.M.Yagupolskii, M.M.Kremlev. Polyfluoromethine compounds - a new type of conjugated systems// Ukr. Khim.Zh. - 1989.- Vol. 55, N 9.- p. 943-955.
12.L.M.Yagupolskii, S.V.Pazenok. Fluoro-containing cyanine dyes.// Zh. Nauchoii i Prilladn. Fotografii i Kinematografii.- 1990.- Vol. 34.- p. 439-448.
13.V.N.Boiko. Nucleophilic substitution at aromatic compounds with fluoro-containing groups.// Izv. Sib.Otd. AN USSR, ser. khim. -1990.-N 1.- p. 126-136.
14.Yu.L.Yagupolskii. Ylides stabilized by (fluoro, perfluoroalkyl)sulfonyl group // Rev. on Heteroatom Chem. (Japan). - 1991.- Vol. 5.- P.136-151.
15.I.I.Maletina, A.A.Mironova, V.V.Orda, L.M.Yagupolskii. Arylperfluoroalkyl - and arylpolyfluoroalkyliodonium salts // Rev. on Heteroatom Chem. (Japan).- 1993.- Vol. 8.- P. 232-255.
16.L.M.Yagupolskii, Yu.L.Yagupolskii. New trends in the chemistry of aromatic compounds with fluorine-containing substituents// J.Fluor.Chem.-1995.-Vol.72. - P.225-229. 

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Research groups of other departments of Institute

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Research group directed by Dr.V. P.Nazaretian

Staff:	Dr.Yu.M.Pustovit, N.I.Liptuha
Research workers:	A.N.Alexeenko, N.D.Volkov, P.I.Ogoiko

Research directions
• reactions of stereochemically defined C3-C6 cycloalcanepolycarboxylic acids with sulfur tetrafluoride
• chemisry of polyfluoroalkanesulfonic acids derivatives;
• investigation of hydrogenization of aromatic and heterocyclic polyfluorinated compounds with hydrogen.
Selected publications
1.Yu.M.Pustovit and V.P.Nazaretian - New views on the fluorination of carbonyl  with SF4.// J.Fluor.Chem.- 1991, v.55, p.29-36;
2.Yu.M.Pustovit, P.I.Ogojko, V.P.Nazaretian, L.B.Faryat’eva - Reactions of cycloalkanecarboxylic acids with SF4. I. Fluorination of cyclopropanepolycarboxylic acids with SF4.// J.Fluor.Chem.-1994, v.69, p.225-229;
3.Yu.M.Pustovit, P.I.Ogojko, V.P.Nazaretian, A.B.Rozhenko - Reactions of cycloalkanecarboxylic acids with SF4. II. Fluorination of gem-dichlorocyclopropanecarboxylic acids with SF4.// J.Fluor.Chem.- 1994, v.69, p.231-236;
4.Yu.M.Pustovit, P.I.Ogojko, V.P.Nazaretian - Reactions of cycloalkanecarboxylic acids with SF4. III. Fluorination of cyclobutane- and cyclopentanetetracarboxylic acids with SF4.// J.Fluor.Chem.- 1994, v.69, p.237-240;
5.Yurii Pustovit, Wojciech Dmowski and Valery Nazaretian.- Fluorocyclization of 2,5-tetrahydrofurandicarboxylic and 2,3,4,5-tetrahydrofurantetracarboxylic acids with sulphur tetrafluoride leading to bicyclic and tricyclic fluoroethers.// J.Fluor.Chem.- 1997, 85 p187-190.
6.A.N.Alekseenko and V.P.Nazaretian - Reactions of cycloalkanecarboxylic acids with SF4. IV. Fluorination of cyclohexanedicarboxylic acids with SF4.// J.Fluor.Chem. 1994, v.69, p. 237-240.
7.A.N.Alekseenko, L.B.Faryat’eva and V.P.Nazaretian Trifluoromethyl derivatives of cyclohexane, Ukr.Khim.Zhurn. 1994, v.60, p.777-785
8. N.D.Volkov, V.P.Nazaretian and  L.M.Yagupolskii -  Halogen  and   Pseudohalogendifluoromethane Sulfonylfluorides - J.Fluor.Chem. 1997, S 96/83, in press).

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Research group directed by Dr.hab.Yu.G.Shermolovich Research directions
• synthesis of polyfluorinated alkoxyphosphoranes, thioaldehydes, thioketones;
• investigation of reactivity and chemical transformations of the polyfluorinated alkoxyphosphoranes, thioaldehydes, thioketones;
• development of convenient methods of synthesis of new types of organophosphorus and organosulphur compounds based on the polyfluorinated alkoxyphosphoranes, tioaldehydes, thioketones.
Selected publications
1. Markovsky L.N., Timoshenko V.M., Rozhenko A.B., Shermolovich Yu.G. One of the reaction of 1,1-dichloropolyfluoroalkylsulphinil chloride with lithium hehamethyl disilylamine.// J.Fluor Chem. 1984, Vol. 66, 7.
2. Markovsky L.N., Kozlov E.S., Shermolovich Yu.G. Polygalogenalkoxy(aryloxy)chloro- and bromophosphoranes.// Heteroatom Chemistry, 1991, Vol. 2, 87.
3. Markovsky L.N., Shermolovich Yu.G., Pinchuk V.A.  at al.Reactions of sulfenamides with compounds of trivalent phosposphorus.//Anorg and Allgem. Chemie. 1995, Bd. 621, 2001.
4. Shermolovich Yu.G., Timoshenko V.M, Markovsky LN. at al.N-Alkyl-C-poluyfluoroalyl chlorosulfinilimides R-C(Cl)=S=N-R.Heteroatom Chemisry, 1995, Vol. 6, 9.

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Research Group directed by Dr.V.E.Pashinnik Research directions
• development of methods of synthesis and investigation of chemical properties of fluorosulfuranes possesing S-O and S-N bonds;
• development of  methods of fluorination of organic compounds by dialkylaminotrifluorosulfuranes (DAST);
• investigation of intermediates in reactions of oxygen containing organic compounds with SF4 and DAST.
Selected publications
1. Markovsky L.N., Pashinnik V.E., Kirsanov A.V. Application of dialkylaminosulfur trifluorides in synthesis of fluoroorganic compounds. // Synthesis, 1973, 787.
2. Markovsky L.N., Pashinnik V.E. Fluorosulfuranes. // Rev. Heteroatom Chem. 1989, Vol. 2, 112.
3. Markovsky L.N., Pashinnik V.P. New fluorination agents in organic synthesis. // Eds. German L.S., Semskov S.V. Berlin, Springer, 1989, p.254.
4. Besuglov V.V., Pashinnik V.E., Markovsky L.N. et all. Stereochemistry of substitution of hydroxyl group on fluorine atom in prostaglandines. Bioorganic Chemistry (Russ.), 1996, Vol. 12, 814.

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Created June 1 1998.

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