Mikhail M. Kremlev

Polyfluoromethine compounds — a new type of conjugated systems

Abstract The methods for synthesis, chemical and physical properties of conjugated α,ω-diarylperfluoropolyenes are described.

Halofluorination of 1,2-difluoro-1,2-di(p-tolyl)ethene, 1,2,3,4-tetrafluoro-1,4-di(p-tolyl) butadiene and its nonfluorinated parent compounds

Abstract The reactions of (E)-1,2-difluoro-1,2-di (p-tolyl) ethene (1) with N-bromo- or N-chlorosuccinimide gave mainly the expected halofluorination products 1-bromo-1,2-di(p-tolyl)-1,2,2-trifluoroethane (2) or 1-chloro-1,2-di(p-tolyl)-1,2,2-trifluoroethane (4), respectively. As a side reaction halogenation of the double bond has been obtained. With (E,E)-1,4-di(p-tolyl)-1,2,3,4-tetrafluorobuta-1,3-diene (6) under the same conditions the products of 1,2- and 1,4-addition or its consecutive hydrolysis products were isolated. (E)-Stilbene (19) on bromofluorination gave solely erythro-1-bromo-2-fluoro-1,2-diphenylethane (20), while with 1,4-diphenylbuta-1,3-diene (17) mainly higher molecular weight products were formed.

Phenyl- and diphenylpolyfluoroolefin epoxides

Abstract The epoxides of α,β,β-trifluorostirene (1), α,β-difluoro-β-chlorostirene (2), 1-phenylperfluoropropene (3) and trans-α,β-difluorostilbene (4) were prepared by oxidation of corresponding ethylenes by oxygene in presence of chlorine under UV-irradiation Investigation of electronic properties of difluorochlorovinyl and difluorochloroepoxiethyl groups has shown their electron accepting nature. The interaction of (1) and (2) with water leads to the formation of phenylglyoxyl fluoride, and the heating of (4) with water gives benzil. The isomerization of (1) and (2) under the action of triethyl amine yields phenyldifluoro- and phenylfluorochloro-acetyl fluorides. Under the action of CsF compounds (1) and (2) are transformed into corresponding ketones. The heating of (4) with gives α-bromo-α-fluorobenzylketone.

CCDC 265521: Experimental Crystal Structure Determination

Related Article: W.Tyrra, M.M.Kremlev, D.Naumann, H.Scherer, H.Schmidt, B.Hoge, I.Pantenburg, Yu.L.Yagupolskii|2005|Chem.-Eur.J.|11|6514|doi:10.1002/chem.200500799