Preparation, NMR, and ab initio/IGLO study of trifluoromethyl-substituted carboxonium ions

Journal of Organic Chemistry

Volumn 61, Issue 6, 1996, Pages 1934-1939

  Olah, George A ^a   Burrichter, Arwed ^a   Rasul, Golam ^a   Yudin, Andrei K ^a   Prakash, G K Surya ^a  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000432233     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9516493     Document Type: Article

References (27)

1. Onium Ions. 45. Part 44: Head, N. J.; Rasul, G.; Mitra, A.; Bashir-Heshimi, A.; Prakash, G. K. S.; Olah, G. A. J. Am. Chem. Soc. 1995, 117, 12107.
2. (a) Perst, H. Oxonium Ions in Organic Chemistry; Verlag Chemie: Weinheim, Germany, 1971.
3. (b) Perst, H. In Carbonium Ions; Olah, G. A., Schleyer, P. v. R., Eds.; Wiley-Interscience: New York, 1976; Vol. 5, pp 1961-2047.
4. (c) Meerwein, H. In Methoden der Organischen Chemie (Houben-Weyl), 4th ed.; Müller, E., Ed.; Thieme: Stuttgart, 1965; Vol. VI/3: Sauerstoffverbindungen, p 329.
5. (d) Olah, G. A.; White, A. M.; O'Brien, D. H. Chem Rev. 1970, 70, 561-591 and references therein.
6. (e) Hartz, N.; Rasul, G.; Olah, G. A. J. Am. Chem. Soc. 1993, 115, 1277-1285 and references therein.
7. For reviews see: (a) Gassman, P. G.; Tidwell, T. T. Acc. Chem. Res. 1983, 16, 279.
8. (b) Creary, X. Chem. Rev. 1991, 91, 1625.
9. (a) Hammett, L. P. J. Am. Chem. Soc. 1937, 59, 96.
10. (b) Johnson, K. F. The Hammett Equation; Cambridge University Press: New York, 1973.
11. Filler, R.; Kobayashi, Y.; Yagupolskii, L. M.; Eds. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications; Elsevier: Amsterdam, 1993.
12. Yoshioka, H.; Nakayama, C.; Matsuo, N. J. Synth. Org. Chem. Jpn. 1984, 42, 809.
13. (a) Kutzelnigg, W. Isr. J. Chem. 1980, 19, 193.
14. (b) Schindler, M.; Kutzelnigg, W. J. Chem. Phys. 1982, 76, 1919.
15. (c) Review: Kutzelnigg, W.; Fleischer, U.; Schindler, M. In NMR. Basic Principles and Progress; Springer Verlag: Berlin, Heidelberg, 1990; Vol. 23, p 165.
16. (a) Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory: John Wiley & Sons. New York, 1986.
17. (b) Lammertsma, K.; Schleyer, P. v. R.; Schwarz, H. Angew. Chem., Int. Ed. Engl. 1989, 28, 1321.
18. (c) Lammertsma, K. Rev. Chem. Intermed. 1988, 9, 141.
19. Olah, G. A.; White, A. M. J. Am. Chem. Soc. 1969, 91, 5801.
20. Drummond, D. F., McMahon, T. B. Int. J. Mass Spectrom Ion Phys. 1977, 25, 27.
21. (a) Krivdin, L. B.; Zinchenko, S. V.; Kalabin, G. A.; Facelli, J. C.; Tufro, M. F.; Contreras, R. H.; Denisov, A. Yu.; Gavrilyuk, O. A.; Mamatyuk, V. I. J. Chem. Soc., Faraday Trans. 1992, 88, 2459-2463.
22. (b) Wiberg, K. B.; Marquez, M.; Castejon, H. J. Org. Chem. 1994, 59, 6817.
23. Olah, G. A.; Parker, D. G.; Yoneda, N.; Pelizza, F. J. Am. Chem. Soc. 1976, 98, 2245.
24. (a) Olah, G. A.; Hartz, N.; Rasul, G.; Burrichter, A.; Prakash, G. K. S. J. Am. Chem. Soc. 1995, 117, 6421.
25. (b) Wiberg, K. B.; Waldron, R. F. J. Am. Chem. Soc. 1991, 113, 7705.
26. Mlsna, T. E.; Lin, W.-H.; Hovsepian, M. M.; Lagow, R. J. Eur. J. Solid State Inorg. Chem. 1992, 29, 907.
27. Gaussian 94 (Revision A.1): Frisch, M. J; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Peterson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 1995.