Intracomplex CH3OH Walking around Optically Active 1-Methyl-3-ethylallyl Cations. A Gas-Phase Kinetic Study

Journal of Organic Chemistry

Volumn 63, Issue 4, 1998, Pages 1012-1019

  Troiani, Anna ^a   Speranza, Maurizio ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542548366     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971282x     Document Type: Article

References (43)

1. Chiral Ions in the Gas Phase. 2. Part 1: Troiani, A.; Gasparrini, F.; Grandinetti, F.; Speranza, M. J. Am. Chem. Soc. 1997, 119, 4525.
2. For reviews, see: (a) Samuel, D.; Silver, B. Adv. Phys. Org. Chem. 1965, 3, 128. (b) Raber, D. J.; Harris, J. M.; Schleyer, P.v. R. Ions and Ion Pairs in Organic Reactions; Szwarc, M., Ed.; Wiley: New York, 1974; Vol. 2.
3. For reviews, see: (a) Samuel, D.; Silver, B. Adv. Phys. Org. Chem. 1965, 3, 128. (b) Raber, D. J.; Harris, J. M.; Schleyer, P.v. R. Ions and Ion Pairs in Organic Reactions; Szwarc, M., Ed.; Wiley: New York, 1974; Vol. 2.
4. Herlihy, K. P. Aust. J. Chem. 1982, 35, 2221.
5. Allen, A. D.; Kanagasabapathy, V. D.; Tidwell, T. T. J. Am. Chem. Soc. 1984, 106, 1361.
6. Dietze, P. E.; Jencks, W. P. J. Am. Chem. Soc. 1987, 109, 2057.
7. Merritt, M. V.; Bronson, G. E.; Baczynskyj, L.; Boal, J. R. J. Am. Chem. Soc. 1980, 102, 346.
8. Merritt, M. V.; Bell, S. J.; Cheon, H. J.; Darlington, J. A.; Dugger, T. L.; Elliott, N. B.; Fairbrother, G. L.; Melendez, C. S.; Smith, E. V.; Schwartz, P. L. J. Am. Chem. Soc. 1990, 112, 3560.
9. Merritt, M. V.; Anderson, D. B.; Basu, K. A.; Chang, I. W.; Cheon, H. J.; Mukundan, N. E.; Flannery, C. A.; Kim, A. Y.; Vaishampayan, A.; Yens, D. A. J. Am. Chem. Soc. 1994, 116, 5551.
10. (a) Thibblin, A. J. Chem. Soc., Perkin Trans. 2 1987, 1987.
11. (b) Thibblin, A. J. Chem. Soc., Chem. Commun. 1990, 697.
12. (c) Thibblin, A. J. Chem. Soc., Perkin Trans. 2 1992, 1195.
13. McAdoo, D. J.; Morton, T. H. Ace. Chem. Res. 1993, 26, 295.
14. An outstanding example of site-specific interactions in ionmolecule complexes is given in: Sunner, J. A.; Hirao, K.; Kebarle, P. J. Phys. Chem, 1989, 93, 4010.
15. Lias, S. G.; Bartmess, J. E.; Liebman, J. F.; Holmes, J. L.; Levin, R. D.; Mallard, W. G. J. Phys. Chem. Ref. Data 1988, 17, Suppl. 1.
16. Coburn, E. R. Organic Syntheses; Wiley: New York, 1955; Collect. Vol. III, p 696.
17. Vogel, A. Textbook of Practical Organic Chemistry; Langman Group Limited: Chapter IIIG, p 413.
18. Luczynsky, Z.; Herman, J. A. J. Phys. Chem. 1978, 82, 1679.
19. Benezra, S. A.; Hoffman, M. K.; Bursey, M. M. J. Am. Chem. Soc. 1970, 92, 7501.
20. Pabst, M. J. K.; Tan, H. S.; Franklin, J. L. Int. J. Mass Spectrom. Ion Phys. 1976, 20, 191.
21. Blint, R. J.; McMahon, T. B.; Beaucharap, J. L. J. Am. Chem. Soc. 1974, 96, 1269.
22. Beauchamp, J. L.; Holtz, D.; Woodgate, S. D.; Patt, S. L. J. Am. Chem. Soc. 1972, 94, 2798.
23. Holtz, D.; Beauchamp, J. L.; Woodgate, S. D. J. Am. Chem. Soc. 1970, 92, 7484.
24. Herod, A. A.; Harrison, A. G.; McAskill, N. A. Can. J. Chem. 1971, 49, 2217.
25. (a) Glukhovtsev, M. N.; Szulejko, J. E.; McMahon, T. B.; Gauld, J. W.; Scott, A. P.; Smith, B. J.; Pross, A.; Radom, L. J. Phys. Chem. 1994, 98, 13099.
26. (b) McMahon, T. B.; Heinis, T.; Nicol, G.; Hovey, J. K.; Kebarle, P. J. Am. Chem. Soc. 1988, 110, 7591.
27. Speranza, M.; Pepe, N.; Cipollini, R. J. Chem. Soc., Perkin Trans. 2 1979, 1179.
28. Pepe, N.; Speranza, M. J. Chem. Soc., Perkin Trans. 2 1981, 1430.
29. Speranza, M.; Angelini, G. J. Am. Chem. Soc. 1980, 102, 3115.
30. Angelini, G.; Speranza, M. J. Am. Chem. Soc. 1981, 103, 3792.
31. Angelini, G.; Speranza, M. J. Am. Chem. Soc. 1981, 103, 3800.
32. Colosimo, M.; Bucci, R. J. Phys. Chem. 1979, 83, 1952.
33. -1 exothermic.
34. -1 exothermic.
35. +, since both lead to the same oxonium intermediate.
36. -1) = 2.04 (40°C); 1.97 (70°C); 1.94 (85°C); 1.92 (100°C); 1.88 (120°C)).
37. (a) Audier, H. E.; Monteiro, C.; Berthomieu, D.; Tortajada, J. Int. J. Mass Spectrom. Ion Proc. 1991, 104, 145.
38. (b) Audier, H. E.; Berthomieu, D.; Morton, T. H. J. Org. Chem. 1995, 60, 7198.
39. 2R'-2s'; Table 1) measured under all experimental conditions and with the observed increase of their ratio with temperature. The same trend excludes the possibility of slow isomerization of the starting IS' to IIR', followed by fast IIR' → IIS' racemization. Analogous arguments apply in regard to the IIR' racemization and regioisomerization pathways.
40. Meot-Ner (Mautner), M.; Karpas, Z.; Deakyne, C. J. Am. Chem. Soc. 1986, 108, 3913.
41. See also: (a) Audier, H. E.; Koyanagi, G. K.; McMahon, T. B.; Tholmann, D. J. Phys. Chem. 1996, 100, 8220. (b) Uggerud, E. J. Am. Chem. Soc. 1994, 116, 6873.
42. See also: (a) Audier, H. E.; Koyanagi, G. K.; McMahon, T. B.; Tholmann, D. J. Phys. Chem. 1996, 100, 8220. (b) Uggerud, E. J. Am. Chem. Soc. 1994, 116, 6873.
43. Meot-Ner (Mautner), M.; Ross, M. M.; Campane, J. E. J. Am. Chem. Soc. 1985, 107, 4839.