Conclusions
-
1.
A study has been made of the formation of aryl(bisarylthio)sulfonium cations from arylsulfenyl chlorides and diaryl disulfides in the presence of SbCl5 or SbF5, using13C NMR. It has been found feasible to use this method to identify stable cations at low temperatures according to the characteristic change in screening of the nuclei of the aromatic carbon atoms.
-
2.
An equilibrium, reversible, intermolecular exchange by SAr groups between the aryl(bisarylthio)sulfonium ions and the original reactants has been detected, this equilibrium exchange depending on the ratio of reactants, the type of solvent, and the temperature.
-
3.
Linear relationships have been found between the13C chemical shifts in these ions and the13C chemical shifts of the corresponding carbon nuclei in Ar2Cl+, Ar3C+, and episulfonium ions and in neutral compounds of the benzene series.
Similar content being viewed by others
Literature cited
C. G. Moore and M. Porter, J. Chem. Soc., 2890 (1958).
F. Pietra and D. Vituli, J. Chem. Soc. B, 623 (1970).
B. Miller and C. H. Han, J. Org. Chem.,36, 1513 (1971).
J. L. Kice, Progr. Inorg. Chem.,17, 147 (1972).
G. Capozzi, V. Lucchini, G. Modena, and R. Rivetti, J. Chem., Soc., Perkin Tr. 2, 900 (1975).
A. S. Gybin, W. A. Smith, V. S. Bogdanov, M. Z. Krimer, and Yu. B. Kal'yan, Summaries from 9th International Symposium on the Chemistry of Organic Compounds [in Russian], Riga (1980), p. 47.
A. S. Gybin, W. A. Smith, V. S. Bogdanov, and M. Z. Krimer, Izv. Akad. Nauk SSSR, Ser. Khim., 1663 (1979).
L. P. Hammett, Physical Organic Chemistry, 2nd edn., McGraw-Hill, New York (1970); T. C. Waddington (editor), Non-Aqueous Solvent Systems, Academic Press, New York (1965).
W. A. Smith, A. S. Gybin, V. S. Bogdanov, M. Z. Krimer, and E. A. Vorobiova, Tetrahedron Lett., 1085 (1978).
G. J. Ray, R. J. Kurland, and A. K. Colter, Tetrahedron,27, 735 (1971).
G. C. Levy and G. L. Nelson, Carbon-13 Nuclear Magnetic Resonance for Organic Chemists, Wiley-Interscience, New York (1972) [p. 168 in Russian translation].
G. A. Olah, T. Sakakibara, and G. Asensio, J. Org. Chem.,43, 463 (1978).
G. A. Olah, P. W. Westermen, and D. A. Forsyth, J. Am. Chem. Soc.,97, 3419 (1975).
G. C. Levy and G. L. Nelson, Carbon-13 Nuclear Magnetic Resonance for Organic Chemists, Wiley-Interscience, New York (1972) [p. 112 in Russian translation].
J. A. Pappas, J. Chem. Soc., Perkin Trans. 2, 67 (1979).
R. R. Fraser, G. Boussard, J. K. Sounders, J. B. Lambert, and C. I. Mixan, J. Am. Chem. Soc.,93, 3822 (1971).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2681–2693, December, 1981.
Rights and permissions
About this article
Cite this article
Bogdanov, V.S., Gybin, A.S., Cherepanova, E.G. et al. 13C NMR spectra of aryl(eisaeylthio) sulfonium ions formed in the reaction of arylsulfenyl chlorides with diaeyl disulfindes in the presence of lewis acids. Russ Chem Bull 30, 2229–2238 (1981). https://doi.org/10.1007/BF00963677
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00963677