Stabilized and Destabilized Carbocations in the 1,6-Methano[10]annulene Series

Journal of Organic Chemistry

Volumn 68, Issue 22, 2003, Pages 8683-8692

  Creary, Xavier ^a   Miller, Kevin ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DELOCALIZAITON;

POSITIVE IONS; SOLVENTS; SUBSTITUTION REACTIONS;

METHANOL;

1,6 METHANO[10]ANNULENE DERIVATIVE; 2 CHLOROMETHYL 1,6 METHANO[10]ANNULENE; 3 CHLOROMETHYL 1,6 METHANO[10]ANNULENE; ANNULENE DERIVATIVE; AROMATIC COMPOUND; CATION; CYCLOHEPTANE DERIVATIVE; CYCLOHEPTATRIENYL CATION; METHANE; METHYL CHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; MOLECULAR STABILITY; SOLVENT EFFECT;

EID: 0142196830     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035006w     Document Type: Article

References (28)

1. (a) Vogel, E.; Roth, H. D. Angew. Chem. Int. Ed. Engl. 1964, 3, 228.
2. (b) Vogel, E.; Klug, W.; Breuer, A Organic Syntheses; Wiley: New York, 1988; Collect. Vol. VI, p 721.
3. Dorn, H. C.; Yannoni, C. S.; Limbach, H. H.; Vogel, E. J. Phys. Chem. 1994, 98, 11628.
4. Creary, X.; Miller, K. Org. Lett. 2002, 4, 3493.
5. Jones, W. M.; LaBar, R. A.; Brinker, U. H.; Gebert, P. H. J. Am. Chem. Soc. 1977, 99, 6379.
6. Neidlein, R.; Zeiner, H. Chem. Ber. 1982, 115, 3353.
7. Kitching, W.; Olszowy, H. A.; Schott, I.; Adcock, W.; Cox, D. P. J. Organomet. Chem. 1986, 310, 269.
8. Nelson, P. H.; Bartsch, G. A.; Untch, K. G.; Fried, J. H. J. Med. Chem. 1975, 18, 583.
9. Winstein, S.; Robinson, G. C. J. Am. Chem. Soc. 1958, 80, 169.
10. Noyce, D. S.; Virgilio, J. A. J. Org. Chem. 1972, 37, 2643.
11. (a) Peters, E. N.; J. Am. Chem. Soc. 1976, 98, 5627.
12. (b) Peters, E. N. J. Org. Chem. 1977, 42, 1419.
13. + value of -4.82 in methanol.
14. For a review and leading references on carbocations containing formal electron-withdrawing groups, see: Creary, X. Chem. Rev. 1991, 91, 1625.
15. Creary, X.; Geiger, C. C. J. Am. Chem. Soc. 1982, 104, 4151.
16. Frisch, M, J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, Jr., J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I. Gomperts, R. ; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
17. Roth, W. R.; Böhm, M.; Lennartz, H. W.; Vogel, E. Angew. Chem., Int. Ed. Engl. 1983, 22, 1007.
18. Vogel, E.; Weyres, F.; Leper, H.; Rautenstrauch, V. Angew. Chem., Int. Ed. Engl. 1966, 5, 732.
19. 5 times more reactive than mesylates or tosylates under solvolytic conditions; see: Su, T. M.; Sliwinski, W. F.; Schleyer, P. v. R. J. Am. Chem. Soc. 1969, 91, 5386.
20. Creary, X.; Burtch, E. A.; Jiang, Z. J. Org. Chem. 2003, 68, 1117.
21. Lustgarten, R. K.; Brookhart, M.; Winstein, S. J. Am. Chem. Soc. 1972, 94, 2347 and references therein.
22. Vogel, E.; Sombroek, J. Tetrahedron Lett. 1974, 17, 1627.
23. Vogel, E.; Böll, W. A.; Biskup, M. Tetrahedron Lett. 1966, 1569.
24. Creary, X. J. Org. Chem. 1987, 52, 5026.
25. Ito, S.; Ohtani, H.; Narita, S.; Honma, H. Tetrahedron Lett. 1972, 2223.
26. Creary, X.; Hatoum, H. N.; Barton, A.; Aldridge, T. J. Org. Chem. 1992, 57, 1887.
27. Creary, X.; Jiang, Z. J. Org. Chem. 1994, 59, 5106.
28. Creary, X.; Wang, Y.-X. J. Org. Chem. 1992, 57, 4762.