Skip to main content
Log in

Thiirenium ions

  • Published:
Reviews of Chemical Intermediates Aims and scope Submit manuscript

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

References and notes

  1. N. Kharasch, in “Organic Sulfur Compounds,” Vol. 1, N. Kharasch, Ed., Pergamon Press, New York (1961); G. H. Schmid and D. G. Garratt, in “The Chemistry of Functional Groups: The Chemistry of Double-bonded Functional Groups, Supplement A,” Part 2, S. Patai, Ed., Wiley, London (1977).

    Google Scholar 

  2. L. Maioli, G. Modena, and F. Taddei,Boll. Sci. Fac. Chim. Ind. Bologna,18, 58 (1960); G. Modena and G. Scorrano,Mechanism of Reaction of Sulfur Compounds,3, 115 (1968).

    CAS  Google Scholar 

  3. For relevant reviews see: G. Modena and U. Tonellato,Adv. Phys. Org. Chem.,9, 185 (1971); P. J. Stang,Progr. Phys. Org. Chem.,10, 205 (1973); L. R. Subramanian and M. Hanack,J. Chem. Educ.,52, 80 (1975); H. G. Richey and J. M. Richey, in “Carbonium Ions,” Vol. 2, G. A. Olah and P. von R. Schleyer, Eds, Wiley, New York (1970).

    Article  CAS  Google Scholar 

  4. C. A. Grob and C. Cseh,Helv. Chim. Acta,47, 194 (1964).

    Article  CAS  Google Scholar 

  5. V. Calo’, G. Modena, and G. Scorrano,J. Chem. Soc., (C),1344 (1968).

  6. A recent report7 claims that M-AM isomerization may occur under strong acidic conditions.

  7. G. H. Schmid, A. Modro, F. Lenz, D. G. Garratt, and K. Yates,J. Org. Chem.,41, 2331 (1976).

    Article  CAS  Google Scholar 

  8. E. Gutschik and V. Prey,Monatsh. Chem.,97, 827 (1961); J. F. Harris, Jr.,J. Am. Chem. Soc.,84, 3148 (1962).

    Article  Google Scholar 

  9. A. Dondoni, G. Modena, and G. Scorrano,Ric. Sci.,34(IIA), 665 (1964). See also Reference 7 G. H. Schmid, A. Modro, F. Lenz, D. G. Garratt, and K. Yates,J. Org. Chem. Chem. Soc.,84, 3148 (1962)

    Google Scholar 

  10. L. Di Nunno, G. Melloni, G. Modena, and G. Scorrano,Tetrahedron Letters, 4405 (1965).

  11. L. Di Nunno, and G. Scorrano,Ric. Sci.,38, 343 (1968).

    Google Scholar 

  12. V. Calo’ and G. Scorrano,Gazz. Chim. Ital.,98, 545 (1968).

    Google Scholar 

  13. V. Calo’, G. Modena, and G. Scorrano,J. Chem. Soc., (C), 1339 (1968).

  14. V. Calo’, G. Scorrano, and G. Modena,J. Org. Chem.,34, 2020 (1969).

    Article  Google Scholar 

  15. G. H. Schmid and M. Heinola,J. Am. Chem. Soc.,90, 3466 (1968).

    Article  CAS  Google Scholar 

  16. A. Dondoni, G. Modena, and G. Scorrano,Boll. Sci. Fac. Chim. Ind. Bologna,22, 26 (1964).

    CAS  Google Scholar 

  17. N. Kharasch and C. N. Yiannios,J. Org. Chem.,29, 1190 (1964).

    Article  CAS  Google Scholar 

  18. E. M. Kosower,J. Am. Chem. Soc.,80, 3253 (1958); K. Dimroth, C. Richardt, T. Siepmann, and F. Bohlmann,Ann.,661, 1 (1963); V. Gutmann,Chemtech,7, 255 (1977).

    Article  CAS  Google Scholar 

  19. (a) G. Capozzi, G. Melloni, and G. Modena,J. Chem. Soc., (C), 2617 (1970); (b)ibid. G. Capozzi, G. Melloni, and G. Modena,J. Chem. Soc., 2621 (1970); (c)ibid. G. Capozzi, G. Melloni, and G. Modena,J. Chem. Soc., 2625 (1970).

  20. G. Modena, U. Tonellato, and F. Naso,Chem. Commun., 1363 (1968).

  21. G. Modena and U. Tonellato,J. Chem. Soc., (B), 374 (1971).

  22. D. S. Noyce, M. A. Matesich, and P. E. Peterson,J. Am. Chem. Soc.,89, 6225 (1967); D. S. Noyce and M. D. Schiavelli,J. Am. Chem. Soc.,90, 1020 (1968); L. L. Miller and D. A. Kaufman,J. Am. Chem. Soc.,90, 7282 (1968); P. Bassi and U. Tonellato,J. Chem. Soc., Perkin II, 1974 (1974).

    Article  CAS  Google Scholar 

  23. G. Modena and U. Tonellato,J. Chem. Soc., (B), 1569 (1971).

  24. G. Modena and U. Tonellato,J. Chem. Soc., (B), 381 (1971).

  25. Z. Rappoport and Y. Apeloig,J. Am. Chem. Soc.,91, 6734 (1969); Z. Rappoport and A. Gal,J. Am. Chem. Soc.,91, 5246 (1969).

    Article  CAS  Google Scholar 

  26. G. Capozzi, G. Melloni, and G. Modena,J. Chem. Soc., (C), 3018, (1971).

  27. A. Burighel, G. Modena, and U. Tonellato,J. Chem. Soc., Perkin II, 2026 (1972).

  28. G. Capozzi, G. Modena, and U. Tonellato,J. Chem. Soc., (B), 1700 (1971).

  29. The scale of stabilities of thiirenium ions, which should be checked by further studies, correlates with the scale of stabilities of cyclopropenium ions.30

  30. R. Breslow, H. Hover, and H. W. Chang,J. Am. Chem. Soc.,84, 3168 (1962); R. C. Kerber and C. M. Hsu,J. Am. Chem. Soc.,95, 3239 (1973).

    Article  CAS  Google Scholar 

  31. G. Modena, G. Scorrano, and U. Tonellato,J. Chem. Soc., Perkin II, 493 (1973).

  32. G. Capozzi and G. Modena,J. Chem. Soc., Perkin I 216 (1972).

  33. G. Capozzi, G. Modena, and L. Ronzini,J. Chem. Soc., Perkin I, 1136 (1972); A. Burighel, G. Modena, and U. Tonellato,J. Chem. Soc., Perkin II, 1021 (1973).

  34. P. Bassi and U. Tonellato,J. Chem. Soc., Perkin II, 1283 (1974).

  35. Z. Rappoport, E. Noy, and Y. Houminer,J. Am. Chem. Soc.,98, 2238 (1976); Y. Houminer, E. Noy, and Z. Rappoport,J. Am. Chem. Soc.,98, 5632 (1976); C. C. Lee and E. C. F. Ko,Can. J. Chem.,54, 3041 (1976).

    Article  CAS  Google Scholar 

  36. G. A. Olah,Angew. Chem. Int. Ed.,12, 173 (1973).

    Article  Google Scholar 

  37. G. Capozzi, V. Lucchini, G. Modena, and F. Rivetti,J. Chem. Soc., Perkin II, 361 (1975).

  38. G. Capozzi, V. Lucchini, G. Modena, and F. Rivetti,J. Chem. Soc., Perkin II, 900 (1975).

  39. G. Capozzi, O. De Lucchi, V. Lucchini, and G. Modena, unpublished results.

  40. G. Capozzi, O. De Lucchi, V. Lucchini, and G. Modena,J. Chem. Soc., Chem. Commun., 248 (1975).

  41. G. Capozzi, V. Lucchini, G. Modena, and P. Scrimin,Tetrahedron Letters, 911 (1977).

  42. R. Destro, T. Pilati, and M. Simonetta,J. Chem. Soc., Chem. Commun., 576 (1977).

  43. G. Capozzi, V. Lucchini, and G. Modena, unpublished results.

  44. G. Capozzi, L. Da Col, V. Lucchini, G. Modena, and G. Valle, unpublished results.

  45. G. Valle, G. Zanotti, and V. Busetti,Cryst. Struct. Comm.,6, 327 (1977).

    CAS  Google Scholar 

  46. (a) I. G. Csizmadia, A. J. Duke, V. Lucchini, and G. Modena,J. Chem. Soc., Perkin II, 1808 (1974); (b) I. G. Csizmadia, F. Bernardi, V. Lucchini, and G. Modena,J. Chem. Soc., Perkin II, 542 (1977).

  47. I. G. Csizmadia, V. Lucchini, and G. Modena,Theoret. Chim. Acta,39, 51 (1975).

    Article  CAS  Google Scholar 

  48. V. Lucchini, G. Modena, and I. G. Csizmadia,Gazz. Chim. Ital.,105, 675 (1975).

    CAS  Google Scholar 

  49. (a) I. G. Csizmadia, V. Lucchini, and G. Modena,Gazz. Chim. Ital., in press; (b) I. G. Csizmadia, V. Lucchini, and G. Modena, unpublished results.

  50. G. Capozzi, O. De Lucchi, V. Lucchini, and G. Modena,Tetrahedron Letters, 2603 (1975).

  51. G. Capozzi, O. De Lucchi, V. Lucchini, and G. Modena,Synthesis,677 (1976).

  52. G. Capozzi, V. Lucchini, G. Modena, and P. Scrimin,Nouv. J. Chim.,2, 95 (1978).

    CAS  Google Scholar 

  53. G. Capozzi, V. Lucchini, G. Modena, and N. Zocca, unpublished results.

  54. S. I. Miller,Advan. Phys. Org. Chem,6, 85 (1968); Z. Rappoport,ibid. Advan. Phys. Org. Chem,7, 1 (1969); G. Modena,Accounts Chem. Res.,4, 75 (1971).

    Google Scholar 

  55. V. Gold,J. Chem. Soc., 1430 (1951); D. R. Kelsey and R. G. Bergman,J. Am. Chem. Soc.,93, 1953 (1971).

  56. R. H. Summerville and P. von R. Schleyer,J. Am. Chem. Soc.,96, 1110 (1974).

    Article  CAS  Google Scholar 

  57. G. Modena, F. Rivetti, and U. Tonellato,J. Org. Chem.,43, 1521 (1978).

    Article  CAS  Google Scholar 

  58. K. Yates, G. H. Schmid, T. W. Regulski, D. G. Garrat, H. V. Leung, and R. McDonald,J. Am. Chem. Soc.,95, 160 (1973) and references cited therein.

    Article  CAS  Google Scholar 

  59. T. Yamabe, S. Nagata, K. Akagi, R. Hashimoto, C. Yamashita, K. Fukui, A. Ohno, and K. Nakamura,J. Chem. Soc., Perkin II, 1516 (1977).

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Capozzi, G., Lucchini, V. & Modena, G. Thiirenium ions. Reviews of Chemical Intermediates 2, 347–375 (1979). https://doi.org/10.1007/BF03156004

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF03156004

Keywords

Navigation