Dimers of .alpha.,.beta.,.beta.-trifluorostyrene

Abstract

Society, and the Shell Corporation for support of this work.(6) All compounds exhibited satisfactory spectral and physical properties. The stereochemistry of intermediates 3 and 4 follows from their 100-MHz nmr spectra.(7) The yields reported are for isolated products. (8) Similar sulfoxide to olefin transformations have been recently reported by B. M. Trost and T. N. Salzmann, J. Amer. Chem. Soc., in press. We thank Professor Trost for communicating an account of this work to us prior to its publication.

Palladium-Catalyzed Cross-Coupling Reactions of Perfluoro Organic Compounds

“…In particular, each reaction step in the cross-coupling of TFE with arylmetal reagents to give trifluorovinylarenes had to occur at a relatively low temperature, since the undesired side-reactions of the resultant trifluorovinylarenes gave a complex mixture. In fact, the [2 + 2] cyclodimerization of (α,β,β-trifluoro)styrene occurred in a head-to head manner at 80 °C to give a mixture of cis and trans isomers [27,67]. Therefore, 3 was reacted with a stoichiometric amount of ZnPh 2 (4a) to determine if the expected reaction would occur at room temperature to give (α,β,β-trifluoro)styrene (5a).…”

Fluoropolymers for Proton Exchange Membranes

“…The synthesis of p-sulfonic acid-α,β,β-trifluorostyrene was patented by the Ballard Power System Company [78] (Fig. It has been shown that dimers or dienes can be prepared by a cyclodimerization reaction of TFS [80][81][82]. First, the action of chlorosulfonic acid onto iodobenzene was achieved from the Sanecki's synthesis [79] and the chlorosulfonate or fluorosulfonate trifluorostyrene compound was obtained via the Burton reaction [77].…”

Visible-Transparent Aromatic Polymers Obtained by the Polycondensation of a Bis(trifluorovinyl)benzene with Bisphenols

“…Such main chain aromatic polymers are expected to show improved material properties including high thermal stability and mechanical strength. However, the polycondensation of bis­(trifluorovinyl)­arene derivatives with bifunctional monomers (e.g., bisphenols) has not appeared so far, probably because the facile [2 + 2] cyclodimerization of the trifluorovinylarens competes with the desired polycondensation reactions. , Very recently, Tosoh Finechem Corp. developed new bis­(trifluorovinyl)­arene compounds bearing ortho-substituents to the trifluorovinyl moieties with very high thermal stability . For example, 2,5-dimethoxy-1,4-bis­(trifluorovinyl)­benzene ( 1 ) was stable up to 180 °C in contrast to the ortho-substituent-free reference compound, 1,4-bis­(trifluorovinyl)­benzene, which underwent a thermal [2 + 2] cycloaddition of the trifluorovinyl moieties around 90 °C.…”