Abstract
The reactions of 2,4-dinitrobenzenesulfenyl chloride with cyclohexene and allylbenzene in formic acid were studied. In this solvent, the reaction yields solvo-adducts and the products of addition of the reagent to the double bond. The reaction follows kinetics of the second order, first order with respect to each reagent. The hydrogen chloride evolved in the reaction has no effect on the overall rate of the process but sharply decreases the rate of accumulation of solvo-adducts due to the common ion effect. In the reaction with allylbenzene, the yield of the solvo-adduct can vary under the action of HCl from 88% at low degrees of reagent conversion to 30% when the reaction is complete.
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N. S. Zefirov, N. K. Sadovaya, L. A. Novgorodtseva, and I. V. Bodrikov,Zh. Org. Khim., 1978,14, 1806 [J. Org. Chem. USSR, 1978,14 (Engl. Transl.)].
N. S. Zefirov, N. K. Sadovaya, L. A. Novgorodtseva, and I. V. Bodrikov,Tetrahedron, 1978,34, 1373.
G. A. Nisnevich, V. I. Mamatyuk, V. A. Barkhash, T. N. Velikokhat'ko, N. K. Sadovaya, N. S. Zefirov, O. I. Lyubinskaya, G. S. Mikoelyan, V. A. Smit, E. Yu. Grudzinskaya, E. V. Skorobogatova, V. R. Kartashov, T. I. Novikova, and I. V. Bodrikov,Zh. Org. Khim., 1990,26, 84 [J. Org. Chem. USSR, 1990,26 (Engl. Transl.)].
C. Brown and D. R. Hogg,J. Chem. Soc. B, 1968, 1262.
T. W. Bently and P. R. Schleyer,J. Am. Chem. Soc., 1976,98, 7658, 7667.
S. T. Entelis and S. T. Tiger,Kinetika reaktsii v zhidkoi faze. Kolichestvennyi uchet vliyaniya sredy [Kinetics of Reactions in Liquid Phase. Quantitative Account for Medium Effect], Khimiya, Moscow, 1973, 413 pp. (in Russian).
I. V. Bodrikov, T. S. Ganzhenko, N. S. Zefirov, and V. R. Kartashov,Dokl. Akad. Nauk SSSR, 1976,226, 831 [Dokl. Chem., 1976,226 (Engl. Transl.)]; T. S. Ganzhenko, Ph. D. (Chem.) Thesis, A. A. Zhadanov Gor'kii Polytechnical Institute, Gor'kii, 1977 (in Russian).
V. R. Kartashov, E. V. Skorobogatova, E. Yu. Grudzinskaya, and N. S. Zefirov,Zh. Org. Khim., 1988,24, 2473 [J. Org. Chem. USSR, 1988.24 (Engl. Transl.)].
A. Weissberger, E. Proskauer, J. Riddick, and E. Toops,Organic Solvents. Physical Properties and Methods of Purification, Interscience Publishers, New York, 1955.
Weygand-Hilgetag,Organisch-chemische Experimentkunst, Johann Ambrosius Barth, Leipzig, 1964.
G. H. Schmid and V. M. Csizmadia,Int. J. Sulf. Chem., 1973,8, 433.
E. Yu. Grudzinskaya and E. V. Skorobogatova,Zh. Org. Khim., 1986,22, 1905 [J. Org. Chem. USSR, 1986,22 (Engl. Transl.)].
N. A. Izmailov, inElektrokhimiya rastvorov [Electrochemistry of Solutions], Khimiya, Moscow, 1976, 281 (in Russian); R. Beits,Opredelenie pH. Teoriya i praktika [Determination of pH. Theory and Practice], Khimiya, Leningrad, 1968, 400 pp. (Russ. Transl.).
R. V. Khoffman,Mekhanizmy khimicheskikh reaktsii [Mechanisms of Chemical Reactions], Khimiya, Moscow, 1979, 300 pp. (Russ. Transl.).
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 95–100, January, 1997.
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Skorobogatova, E.V., Shalin, S.K., Kartashov, V.R. et al. The common ion effect in sulfenylhalogenation of alkenes in formic acid. Russ Chem Bull 46, 90–95 (1997). https://doi.org/10.1007/BF02495354
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DOI: https://doi.org/10.1007/BF02495354