The [C6H10]·+ hypersurface: The parent radical cation Diels-Alder reaction

Journal of the American Chemical Society

Volumn 121, Issue 28, 1999, Pages 6719-6729

  Hofmann, Matthias ^a   Schaefer III, Henry F ^a  

^a UNIVERSITY OF GEORGIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE DERIVATIVE; CYCLOHEXENE DERIVATIVE; ETHYLENE;

ARTICLE; CATALYSIS; CYCLIZATION; REACTION ANALYSIS; STEREOSPECIFICITY; SYNTHESIS;

EID: 0033591939     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983338q     Document Type: Article

References (49)

1. Müller, F.; Mattay, J. Chem. Rev. 1993, 93, 99.
2. Bauld, N. L. J. Am. Chem. Soc. 1992, 114, 5800.
3. Hintz, S.; Heidbreder, A.; Mattay, J. Top. Curr. Chem. 1996, 177, 77.
4. For a review see: Bauld, N. L. Tetrahedron 1989, 45, 5307.
5. Houk, K. N. Acc. Chem. Res. 1975, 8, 361.
6. Fleming, I. Frontier orbitals and organic chemical reactions, Wiley: New York, 1977.
7. Bellville, D. J.; Bauld, N. L. J. Am. Chem. Soc. 1981, 103, 718.
8. Schmittel, M.; von Seggern, H. Angew. Chem. 1991, 103, 981.
9. Schmittel, M.; von Seggern, H. J. Am. Chem. Soc. 1993, 115, 2165.
10. (a) Gieseler, A.; Steckhan, E.; Wiest, O. Synlett 1990, 275.
11. (b) Wiest, O.; Steckhan, E.; Grein, F. J. Org. Chem. 1992, 57, 4034.
12. (a) Schmittel, M.; Wöhrle, C. Tetrahedron Lett. 1993, 34, 8431.
13. (b) Schmittel, M.; Wöhrle, C. J. Org. Chem. 1995, 60, 8223.
14. Schmittel, M.; Wöhrle, C.; Bohn, I. Chem. Eur. J. 1996, 2, 1031.
15. Woodward, R. B.; Hoffmann, R. Angew. Chem. 1969, 81, 797; Angew. Chem., Int. Ed. Engl. 1969, 8, 781.
16. Woodward, R. B.; Hoffmann, R. Angew. Chem. 1969, 81, 797; Angew. Chem., Int. Ed. Engl. 1969, 8, 781.
17. Bellville, D. J.; Bauld, N. L. J. Am. Chem. Soc. 1982, 104, 2665.
18. Bauld, N. L.; Bellville, D. J.; Pabon, R.; Chelsky, R.; Green, G. J. Am. Chem. Soc. 1983, 105, 2378.
19. Mlcoch, J.; Steckhan, E. Tetrahedron Lett. 1987, 28, 1081.
20. Chokalingam, K.; Pinto, M.; Bauld, N. L. J. Am. Chem. Soc. 1990, 112, 447.
21. Bauld, N.; Bellville, D. F.; Harirchian, B.; Lorenz, K.; Pabon, R. A.; Reynolds, D. W.; Wirth, D. D.; Chiou, H.-S.; Marsh, B. K. Acc. Chem. Res. 1987, 20, 371.
22. A distonic radical cation has separated radical and cation centers.
23. Clark, T. Top. Curr. Chem. 1996, 177, 1.
24. (a) Jungwirth, P.; Cársky, P.; Bally, T. J. Am. Chem. Soc. 1993, 115, 5776.
25. (b) Jungwirth, P.; Bally, T. J. Am. Chem. Soc. 1993, 115, 5783.
26. Pabon, R. A.; Bauld, N. L. J. Am. Chem. Soc. 1984, 706, 1145.
27. Bouchoux, G.; Salpin, J.-Y. Rapid Commun. Mass Spectrom. 1994, 8, 325.
28. Derrick, P. J.; Fallick, A. M.; Burlingame, A. L. J. Am. Chem. Soc. 1972, 94, 6794.
29. Haberl, U.; Wiest, O.; Steckhan, E. J. Am. Chem. Soc., 1999, 121, 6730-6736.
30. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. 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. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94; Gaussian, Inc.; Pittsburgh, PA, 1995, Revision C.3.
31. (a) Huzinaga, S. J. Chem. Phys. 1965, 42, 1293.
32. (b) Dunning, T. H. J. Chem. Phys. 1970, 53, 2823.
33. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
34. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B: Solid State 1988, 37, 785.
35. Stephens, P. J.; Devlin, F. J.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623.
36. Bally, T.; Sastry, G. N. J. Phys. Chem. A 1997, 101, 7923.
37. (a) Purvis, G. D.; Bartlett, R. J. J. Chem. Phys. 1982, 76 1910.
38. (b) Rittby, M.; Bartlett, R. J. J. Phys. Chem. 1988, 92, 3033.
39. Reed, A. E.; Weinhold, F. Chem. Rev. 1988, 88, 899.
40. Bellville, D. J.; Bauld, N. L Tetrahedron 1986, 42, 6167.
41. -1 energy difference (CCSD(T)/ DZP//UMP2(fc)/DZP + 0.93 ZPE(UMP2(fc)/DZP)) for the following reaction: allyl radical + methyl cation → allyl cation + methyl radical. Attempts to optimize the geometry for an open chain distonic radical cation with a primary carbocation center at C6 and a C1-C2-C3 allylic moiety resulted in a proton moving from C5 to C6.
42. Frey, H. M.; Pottinger, R. J. Chem. Soc., Faraday Trans. 1 1978, 1827.
43. Reynolds, D. W.; Harirchian, B.; Chiou, H.-S.; Marsh, B. K.; Bauld, N. L. J. Phys. Org. Chem. 1989, 2, 57.
44. Kim, T.; Pye, R. J.; Bauld, N. L. J. Am. Chem. Soc. 1990, 112, 6285.
45. Bauld, N. L. J. Comput. Chem. 1990, 11, 896.
46. While we were able to reproduce the data on 7 at UHF/3-21G, our results differ from the geometric parameters and the absolute energies reported for 10 and TS-6/10 in ref 39. The method and programs used in that work were not described fully.
47. Murcko, M. A.; Castejon, H.; Wiberg, K. B. J. Phys. Chem. 1996, 100, 16162.
48. Sastry, G. N.; Bally, T.; Hrouda, V.; Cársky, P. J. Am. Chem. Soc. 1998, 120, 9323.
49. Hofmann, M.; Schaefer, H. F. J. Phys. Chem., submitted for publication.