The 2-norbornyl cation: A retrospective

Journal of Physical Organic Chemistry

Volumn 27, Issue 5, 2014, Pages 374-379

  Moss, Robert A ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

calculations; carbocations; ion pairs; isotope effects; NMR; thermochemistry; X ray crystallography

Indexed keywords

CALCULATIONS; ISOTOPES; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SELF ASSEMBLY; THERMOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

CARBOCATIONS; CARBON CARBONS; CARBON COMPOUNDS; ELECTRON DONORS; ION PAIRS; ISOTOPE EFFECT;

POSITIVE IONS;

EID: 84898796913     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.3290     Document Type: Article

References (43)

1. F. Scholz, D. Himmel, F. W. Heinemann, P. v. R. Schleyer, K. Meyer, I. Krossing, Science 2013, 341, 62-64.
2. Some background references of both chemical and historical interest: a), P. D. Bartlett, Nonclassical Ions, Benjamin, New York, 1965
3. b) H. C. Brown, The Nonclassical Ion Problem, with comments by P. v. R. Schleyer, Springer, New York, 1977
4. c) C. A. Grob, Acc. Chem. Res. 1983, 16, 426-431
5. d) H. C. Brown, Acc. Chem. Res. 1983, 16, 432-440
6. e) G. A. Olah, G. K. Surya Prakash, M. Saunders, Acc. Chem. Res. 1983, 16, 440-448
7. f) C. Walling, Acc. Chem. Res. 1983, 16, 448-454
8. g) G. A. Olah, Angew. Chem. Int. Ed. Engl. 1995, 34, 1393-1405
9. h) G. A. Olah, J. Org. Chem. 2001, 66, 5943-5957.
10. S. Winstein, D. Trifan, J. Am. Chem. Soc. 1949, 71, 2953.
11. S. Winstein, D. Trifan, J. Am. Chem. Soc. 1952, 74, 1147-1154.
12. S. Winstein, D. Trifan, J. Am. Chem. Soc. 1952, 74, 1154-1160.
13. T. W. Bentley, C. T. Bowen, D. H. Morten, P. v. R. Scheyer, J. Am. Chem. Soc. 1981, 103, 5466-5475.
14. W. Kirmse, E. Herpers, Angew. Chem. Int. Ed. Engl. 1991, 30, 1018-1020.
15. R. A. Moss, F. Zheng, R. R. Sauers, J. P. Toscano, J. Am. Chem. Soc. 2001, 123, 8109-8116.
16. L. Ma, E. H. Sweet, P. G. Schultz, J. Am. Chem. Soc. 1999, 121, 10227-10228.
17. B. L. Murr, A. Nickon, T. D. Swartz, N. H. Werstiuk, J. Am. Chem. Soc. 1967, 89, 1730-1732.
18. J. M. Jerkunica, S. Borcic, D. E. Sunko, Chem. Comm. 1967, 1302-1304.
19. For an alternative analysis of these isotope effects see:, S. Scheppele, Chem. Rev. 1972, 72, 511-532.
20. H. C. Brown, Tetrahedron 1976, 32, 179-204.
21. J. J. Solomon, F. H. Field, J. Am. Chem. Soc. 1976, 98, 1567-1569.
22. E. M. Arnett, C. Petro, J. Am. Chem. Soc. 1978, 100, 5408-5416.
23. Similar conclusions are reached from comparative calorimetric studies of the rearrangements of sec- to tert-2-norbornyl cations versus 2-butyl to t-butyl cations. The norbornyl rearrangement is ~7.5 kcal/mol less exoergonic than the sec- to t-butyl rearrangement, a difference attributed to "extra stabilization" in the 2-norbornyl cation:, E. M. Arnett, N. Pienta, C. Petro, J. Am. Chem. Soc. 1980, 102, 398-400.
24. a) M. Saunders, P. v. R. Schleyer, G. A. Olah, J. Am. Chem. Soc. 1964, 86, 5680-5681
25. b) G. A. Olah, A. M. White, J. R. DeMember, A. Commeyras, C. Y. Lui, J. Am. Chem. Soc. 1970, 92, 4627-4640
26. c) G. A. Olah, G. K. Surya Prakash, M. Arvanaghi, F. A. L. Anet, J. Am. Chem. Soc. 1982, 104, 7105-7108.
27. P. v. R. Schleyer, W. E. Watts, R. C. Fort, Jr., M. B. Comisarow, G. A. Olah, J. Am. Chem. Soc. 1964, 86, 5680-5681.
28. a) C. S. Yanoni, V. Macho, P. C. Myrhe, J. Am. Chem. Soc. 1982, 104, 907-909
29. b) C. S. Yanoni, V. Macho, P. C. Myrhe, J. Am. Chem. Soc. 1982, 104, 7380-7381
30. c) P. C. Myrhe, G. G. Webb, C. S. Yanoni, J. Am. Chem. Soc. 1990, 112, 8991-8992.
31. M. Saunders, M. R. Kates, J. Am. Chem. Soc. 1980, 102, 6867-6868.
32. For a detailed discussion, see, T. H. Lowry, K. S. Richardson, Mechanism and Theory in Organic Chemistry, 3rd Edition, Harper & Row, New York, 1987, pp 475-477.
33. a) G. A. Olah, G. D. Mateescu, J. L. Riemenschneider, J. Am. Chem. Soc. 1972, 94, 2529-2530
34. b) G. A. Olah, G. Liang, G. D. Mateescu, J. L. Riemenschneider, J. Am. Chem. Soc. 1973, 95, 8698-8702.
35. G. M. Kramer, Adv. Phys. Org. Chem. 1975, 11, 177-224.
36. D. T. Clark, B. J. Cromarty, L. Colling, J. Am. Chem. Soc. 1977, 99, 8120-8121.
37. a) T. Laube, Angew. Chem. Int. Ed. Engl. 1987, 26, 560-562
38. b) T. Laube, Acc. Chem. Res. 1995, 28, 399-405.
39. For an excellent analysis, see, D. Lenoir, Y. Apeloig, D. Arad, P. v. R. Schleyer, J. Org. Chem. 1988, 53, 661-675.
40. W. Koch, B. Liu, D. J. DeFrees, J. Am. Chem. Soc. 1989, 111, 1527-1528.
41. P. v. R. Schleyer, S. Sieber, Angew. Chem. Int. Ed. 1993, 32, 1606-1608.
42. P. R. Schreiner, D. L. Severance, W. L. Jorgensen, P. v. R. Schleyer, H. F. Schaefer, III, J. Am. Chem. Soc. 1995, 117, 2663-2664.
43. S. A. Perera, R. J. Bartlett, J. Am. Chem. Soc. 1996, 118, 7849-7850.