Abstract
The electrochemical reduction of a number of polyfluorovinyl halides RCF=CFX (R =t-C4F9, X = F, Cl, Br; R = Ph, X = F, Cl) has been studied by the cyclic voltammetry technique using various different electrodes. An unusual tendency toward hampering of the reduction was observed on going from X = F to a heavier halogen. Calculations of the energies of the molecular orbitals for these compounds were carried out by the AM I method. A mechanism of the reduction of polyfluorovinyl halides was suggested on the basis of correlations between the values of the reduction potentialsE Red and the LUMO energies.
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References
Z. Rappoport,Acc. Chem. Res., 1981,14, 7.
K. P. Butin, A. A. Ivkina, V. N. Shishkin, B. S. Tanaseichuk, and O. A. Reutov,Izv. Akad. Nauk SSSR, Ser. Khim., 1983,98 1 [Bull. Acad. Sci. USSR, Div. Chem. Sci.], (in Russian).
K. P. Butin, A. A. Mina, and V. N. Shishkin,Zh. Org. Khim., 1985,21, 150 [J. Organ. Chem. USSR, 1985, 21 (Engl. Transl.)].
L. L. Kukhareva, T. V. Magdesieva, G. A. Artamkina, L. P. Beletskaya, and K. P. Butin,Izv. Akad. Nauk, Ser. Khim., 1996, 1523 [Russ. Chem. Bull., 1996,45, 1425 (Engl. Transl.)]
A. L. Fry and M. A. Mitnick,J. Am. Chem. Soc., 1969,91, 6207.
L. L. Miller and E. Riekena,J. Org. Chem., 1969,34, 3359.
G. Le Guillanton and A. Daver, Bull. Soc. Chim. Fr., 1973, 724.
N. Gatti, W. Jugelt, and H. Lund,Acta Chem. Scand. Ser. B, 1987,B41(9), 646.
P. J. Elving, I. Rosental, J. R. Hayes, and A. J. Martin,Analyt. Chem., 1961,33, 330.
J. M. Savcant,Adv. Phys. Org. Chem., 1990,26, 1.
C. Corvaja, G. Farnia, G. Formenton, W. Navarrini, G. Sandona, and V. Tortelli,J. Phys. Chem., 1994,98, 2307.
L. Libit and R. Hoffman,J. Am. Chem. Soc., 1974,96, 1370.
Organic Electrochemistry, Eds. Manuel M. Baizer and H. Lund, Marcel Dekker, New York, 1983.
T. V. Magdcsicva, V. N. Shishkin, and K. P. Butin,Zh. Obshch. Khim. 1991,61, 2403 (J. Gen. Chem. USSR, 1991, 61 (Engl. Transi.)).
A. J. Gordon and R. A. Ford,The Chemist's Companion, Wiley, New York, 1972.
A. J. Hoefnagel and E. M. Wepster,J. Am. Chem. Soc., 1973,95, 5357.
S. Ehrenson,Progr. Phys. Org. Chem., 1964,2, 195.
S. Ehrenson, R. T. C. Brownlee, and R. W. Taft,Progr. Phys. Org. Chem., 1973,10, 1.
R. W. Taft, E. Prince, I. R. Fox, I. C. Lewis, K. K. Anderson, and G. T. Devis,J. Am. Chem. Soc., 1963,85, 3146.
M. Charton and H. Meisllich,J. Am. Chem. Soc., 1958,80, 5940.
B. J. Arnold, P. G. Sammes, and T. W. Wallace,J. Chem. Soc., Perkin,1, 1974, 409.
C. P. Andrieux, P. Hapiot, and J. M. Savcant,Chem, Rev., 1990,90, 723.
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1436–1445, June, 1996.
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Butin, K.P., Magdesieva, T.V., Kukhareva, I.I. et al. Electrochemical investigation of the redox properties of some polyfluorinated alkenes. The influence of electrode materials on the shape of polarization curves. Russ Chem Bull 45, 1366–1375 (1996). https://doi.org/10.1007/BF01434214
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DOI: https://doi.org/10.1007/BF01434214