Production of carbenium ions from carbenes by protonation

Pure and Applied Chemistry

Volumn 70, Issue 10, 1998, Pages 2031-2038

  Steenken, Steen ^a  

^a MAX PLANCK INSTITUTE FOR CHEMICAL ENERGY CONVERSION   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0009155441     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac199870102031     Document Type: Article

References (36)

1. nd ed, Cornell University Press, 1973. c) Kresge, .J In Proton Transfer Reactions, Caldin, E.F.; Gold, V., Eds, Chapman and Hall, 1975. d) Bernasconi, C.F. Acc. Chem. Res. 1987, 20, 301.
2. nd ed, Cornell University Press, 1973. c) Kresge, .J In Proton Transfer Reactions, Caldin, E.F.; Gold, V., Eds, Chapman and Hall, 1975. d) Bernasconi, C.F. Acc. Chem. Res. 1987, 20, 301.
3. nd ed, Cornell University Press, 1973. c) Kresge, .J In Proton Transfer Reactions, Caldin, E.F.; Gold, V., Eds, Chapman and Hall, 1975. d) Bernasconi, C.F. Acc. Chem. Res. 1987, 20, 301.
4. nd ed, Cornell University Press, 1973. c) Kresge, .J In Proton Transfer Reactions, Caldin, E.F.; Gold, V., Eds, Chapman and Hall, 1975. d) Bernasconi, C.F. Acc. Chem. Res. 1987, 20, 301.
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17. Yates, P.; Loutfy, R.O. Acc. Chem. Res. 1975, 8, 209.
18. The ring expansion proceeds from the singlet state, see a) Hopkinson, A.C., Lee-Ruff, E., Lien, M.H. Tetrahedron 1988, 44, 6815. b) Morton, D.R.; Turro, N.J. J. Am. Chem. Soc. 1973, 95, 3947. c) The ring expansion (Φ 0.1-0.2) is the only photochemical reaction.
19. The ring expansion proceeds from the singlet state, see a) Hopkinson, A.C., Lee-Ruff, E., Lien, M.H. Tetrahedron 1988, 44, 6815. b) Morton, D.R.; Turro, N.J. J. Am. Chem. Soc. 1973, 95, 3947. c) The ring expansion (Φ 0.1-0.2) is the only photochemical reaction.
20. The ring expansion proceeds from the singlet state, see a) Hopkinson, A.C., Lee-Ruff, E., Lien, M.H. Tetrahedron 1988, 44, 6815. b) Morton, D.R.; Turro, N.J. J. Am. Chem. Soc. 1973, 95, 3947. c) The ring expansion (Φ 0.1-0.2) is the only photochemical reaction.
21. Quinkert, G.; Kaiser, K.H.; Stohrer, W.-D. Angew. Chem. Int. Ed. Engl. 1974, 13, 198. Stohrer, W.-D.; Jacobs, P.; Kaiser, K.H.; Quinkert, G. Top. Curr. Chem. 1974, 46, 181.
22. Quinkert, G.; Kaiser, K.H.; Stohrer, W.-D. Angew. Chem. Int. Ed. Engl. 1974, 13, 198. Stohrer, W.-D.; Jacobs, P.; Kaiser, K.H.; Quinkert, G. Top. Curr. Chem. 1974, 46, 181.
23. The same spectrum is seen in cyclohexane solution. However, here the lifetime is only 6 μs.
24. Quinkert, G.; Kaiser, K.H.; Stohrer, W.-D. Angew. Chem. Int. Ed. Engl. 1974, 13, 198. Stohrer, W.-D.; Jacobs, P.; Kaiser, K.H.; Quinkert, G. Top. Curr. Chem. 1974, 46, 181.
25. Quinkert, G.; Kaiser, K.H.; Stohrer, W.-D. Angew. Chem. Int. Ed. Engl. 1974, 13, 198. Stohrer, W.-D.; Jacobs, P.; Kaiser, K.H.; Quinkert, G. Top. Curr. Chem. 1974, 46, 181.
26. Matsumura, M.; Ammann, J.R.; Sheridan, R.S. Tetrahedron Lett. 1992, 33, 1843.
27. Bethell, D.; Newall, A.R.; Whittaker, D. J. Chem. Soc. B 1971, 23. Zupancic, J.J.; Grasse, P.B.; Lapin, S.C.; Schuster, G.B: Tetrahedron 1985, 41, 1471. Warner, P.M.; Chu, I.S.; J. Am. Chem. Soc. 1984, 106, 5366; J. Org. Chem. 1984, 49, 3666.
28. Bethell, D.; Newall, A.R.; Whittaker, D. J. Chem. Soc. B 1971, 23. Zupancic, J.J.; Grasse, P.B.; Lapin, S.C.; Schuster, G.B: Tetrahedron 1985, 41, 1471. Warner, P.M.; Chu, I.S.; J. Am. Chem. Soc. 1984, 106, 5366; J. Org. Chem. 1984, 49, 3666.
29. Bethell, D.; Newall, A.R.; Whittaker, D. J. Chem. Soc. B 1971, 23. Zupancic, J.J.; Grasse, P.B.; Lapin, S.C.; Schuster, G.B: Tetrahedron 1985, 41, 1471. Warner, P.M.; Chu, I.S.; J. Am. Chem. Soc. 1984, 106, 5366; J. Org. Chem. 1984, 49, 3666.
30. Bethell, D.; Newall, A.R.; Whittaker, D. J. Chem. Soc. B 1971, 23. Zupancic, J.J.; Grasse, P.B.; Lapin, S.C.; Schuster, G.B: Tetrahedron 1985, 41, 1471. Warner, P.M.; Chu, I.S.; J. Am. Chem. Soc. 1984, 106, 5366; J. Org. Chem. 1984, 49, 3666.
31. The spectrum shown is not corrected for depletion of parent. Thus, the two observed maxima at the wings of the absorption band of the parent may only be apparent ones.
32. In HFIP, the lifetime of the cation is ≈ 20 times larger than in TFE.
33. Moss, R.A.; Shen, S.; Wlostowski, M. Tetrahedron Lett. 1988, 29, 6417.
34. 2O. It is obvious that a more polar solvent should favor a reaction in which neutral reagents are converted into ionic products.
35. McClelland, R.A.; Banait, N.; Steenken, S. J. Am. Chem. Soc. 1986, 108, 7023. Albrecht, E.; Mattay, J.; Steenken, S. J. Am. Chem. Soc 1997, 119, 11605.
36. McClelland, R.A.; Banait, N.; Steenken, S. J. Am. Chem. Soc. 1986, 108, 7023. Albrecht, E.; Mattay, J.; Steenken, S. J. Am. Chem. Soc 1997, 119, 11605.