Carbodications. 4.1 Hydrogen Isotope Exchange of Crotonyl Cations in Superacid

Journal of Organic Chemistry

Volumn 61, Issue 25, 1996, Pages 8860-8865

  Fǎrcaşiu, Dan ^a   Bologa, Ursula L ^a  

^a University of Pittsburgh   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001012017     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960889v     Document Type: Article

References (36)

1. For the previous paper in the series, see: Farca§iu, D.; Ghenciu, A. J. Org. Chem. 1991, 56, 6050.
2. On leave during 1993 from the Organic Chemistry Department, Polytechnic University of Bucharest, Romania.
3. (a) Farcasiu, D.; Marino, G.; Miller, G.; Kastrup, R. V. J. Am. Chem. Soc. 1989, 111, 7210 and previous papers cited therein,
4. (b) Farcasiu, D.; Miller, G.; Ghenciu, A. J. Catal. 1992, 134, 118.
5. Farcasiu, D.; Ghenciu, A. Ibid. 1992, 134, 126.
6. Farcasiu, D.; Ghenciu, A. J. Am. Chem. Soc. 1993, 775, 10901.
7. (e) Farcasiu, D., Li, J. Q. J. Phys. Chem. 1994, 98, 6893.
8. (f) Farcasiu, D.; Li, J. J. Catal. 1995, 752, 198.
9. Farcasiu, D.; Miller, G. J. Org. Chem. 1989, 54, 5423.
10. -4 was made; see: Brouwer, D. M.; van Doom, J. A. Red. Trav. Chim. Pays-Bas 1970, 89, 553;
11. 1972, 91, 895.
12. For the analogous HCl elimination converting a 3-chloroalkyl cation to an alkenyl cation, see: Farca§iu, D.; Rich, R.; Rose, K. D. J. Org. Chem. 1989, 54, 4582 and earlier work cited there.
13. Färcasiu, D.; Miller, G.; Sharma, S. J. Phys. Org. Chem. 1990, 3, 639.
14. A kinetic study like this cannot elucidate the actual structure of primary alkylacyl dications (e.g., 3) written here in the conventional representation; we feel that at this stage only theoretical calculations can address such a problem.
15. Hogeveen, H.; Gaasbeek, C. J. Red. Trau. Chim. Pays-Bas 1970, 89, 395.
16. Curtin, D. Y. Rec. Chem. Prog. 1954,15, 111.
17. Furniss, B. S.; Hannaford, A. J.; Rogers, V.; Smith, P. W. G.; Tatchell, A. R. Vogel's Textbook of Practical Organic Chemistry, 4th ed.; Longmans Scientific-John Wiley: New York, 1978; p 512.
18. Färcasiu, D. J. Org. Chem. 1979, 44, 2103.
19. Kogelbauer, A.; Reddick, J.; Färca§iu, D. J. Mol. Catal. 1995, 103, 31.
20. Färcaciu, D.; Ghenciu, A.; Li, J. Q. J. Catal. 1996, 158, 116.
21. Ogata, Y.; Harada, T.; Sugimoto, T. Can. J. Chem. 1977, 55, 1268.
22. Collins, C. J., Bowman, N. S., Eds. Isotope Effects in Chemical Reactions; Van Nostrand-Reinhold: New York, 1970.
23. V. J. Shiner, Jr., in ref 16, pp 90-159, especially pp 129-131, has indicated that β-KIÉ is higher for the heavy isotope in a methylene group than in a methyl group. The difference does not seem large enough, however, to warrant using here two values for this parameter instead of one. The value found should be considered as an average between the two.
24. Fôrcaçiu, D.; Marino, G.; Hsu, C. S. J. Org. Chem. 1994, 59, 163.
25. (a) Creary, X. J. Org. Chem. 1976, 41, 3740.
26. (b) Sunko, D. E.; Szele, I.; Tomic, M. Tetrahedron Lett. 1972, 1827.
27. Gassman, P. G.; Pascone, J. M. J. Am. Chem. Soc. 1973, 95, 7801.
28. (a) Praill, P. F. G.; Saville, B. Chem. Ind. (London) I960, 495.
29. (b) Praill, P. F. G. Acylatlon Reactions: Their Applications and Mechanisms; Pergamon Press: Oxford, 1963.
30. (a) Färcasiu, D.; Miller, G. Unpublished.
31. (b) Miller, G. Ph.D. Thesis, Clarkson University, 1991.
32. Heck, A. J. R.; de Koning, L. J.; Nibbering, N. M. M. J. Am. Soc. Mass. Spectrom. 1991, 2, 453.
33. (a) Westheimer, F. H. Chem. Rev. 1961, 61, 265.
34. (b) Melander, L. Isotope Effects on Reaction Kates; Ronald Press: New York, 1969; pp 24-32.
35. Willi, A. V.; Wolfsberg, M. Chem. Ind. 1964, 2097.
36. Bender, M. L. Mechanism of Homogeneous Catalysis from Protons to Proteins; Wiley-Interscience: New York, 1971; Chapter 4.