Pure Appl. Chem., 2012, Vol. 84, No. 4, pp. 1101-1112
http://dx.doi.org/10.1351/PAC-CON-11-09-08
Published online 2012-02-24
Antiaromatic ions and their value in quantifying aromaticity, as probes of delocalization, and potential as stable diradicals
References
- 1. R. Angew. Chem., Int. Ed. Engl. 33, 1376 (1994). ( , H. Jiao, P. v. R. Schleyer. http://dx.doi.org/10.1002/anie.199413761)
- 2. M. K. J. Org. Chem. 67, 1333 (2002). ( , T. M. Krygowski, A. R. Katritzky, P. v. R. Schleyer. http://dx.doi.org/10.1021/jo016255s)
- 3. M. J. Chem. Educ. 74, 132 (1997). ( . http://dx.doi.org/10.1021/ed074p132)
- 4. M. K. Chem. Rev. 105, 3773 (2005). ( . http://dx.doi.org/10.1021/cr0300845)
- 5. P. v. R. Org. Lett. 4, 2873 (2002). ( , F. Puehlhofer. http://dx.doi.org/10.1021/ol0261332)
- 6. T. M. Chem. Rev. 101, 1385 (2001). ( , M. K. Cyranski. http://dx.doi.org/10.1021/cr990326u)
- 7. J. Tetrahedron Lett. 3839 (1972). ( , T. M. Krygowski. http://dx.doi.org/10.1016/S0040-4039(01)94175-9)
- 8. P. v. R. Pure Appl. Chem. 68, 209 (1996). ( , H. Jiao. http://dx.doi.org/10.1351/pac199668020209)
- 9. R. H. Chem. Rev. 101, 1301 (2001). ( . http://dx.doi.org/10.1021/cr990359+)
- 10. J. A. N. F. Chem. Rev. 101, 1349 (2001). ( , R. B. Mallion. http://dx.doi.org/10.1021/cr990323h)
- 11. H. J. Dauben, D. J. Wilson, J. L. Laity. In Nonbenzenoid Aromaticity, J. P. Snyder (Ed.), pp. 167–180, Academic Press, New York (1971).
- 12. J. Rev. Roum. Chim. 26, 1035 (1981). , O. Ouamerali.
- 13. P. v. R. J. Am. Chem. Soc. 118, 6317 (1996). ( , C. Maerker, A. Dransfeld, H. Jiao, N. J. v. E. Hommes. http://dx.doi.org/10.1021/ja960582d)
- 14. H. Org. Lett. 8, 863 (2006). ( , C. S. Wannere, C. Corminboeuf, R. Puchta, P. v. R. Schleyer. http://dx.doi.org/10.1021/ol0529546)
- 15. Napthalene, phenanthrene, fluoranthrene, tropylium cation, cyclooctatetraene dication.
- 16. A. R. J. Org. Chem. 63, 5228 (1998). ( , M. Karelson, S. Sild, T. M. Krygowski, K. Jug. http://dx.doi.org/10.1021/jo970939b)
- 17. Pentalene, 2, azulene dication, pyrene dication, 9-(1H-indenylidene)-9H-fluorene dication.
- 18. N. S. J. Org. Chem. 72, 9163 (2007). ( , K. B. Llagostera. http://dx.doi.org/10.1021/jo7013609)
- 19. P. Chem.—Eur. J. 12, 8813 (2006). ( , S. Fias, R. Ponec. http://dx.doi.org/10.1002/chem.200600541)
- 20. A. J. Org. Chem. 71, 883 (2006). ( . http://dx.doi.org/10.1021/jo051746o)
- 21. R. M. Tetrahedron Lett. 24, 1139 (1983). ( , L. S. John, B. A. Luxon. http://dx.doi.org/10.1016/S0040-4039(00)86386-8)
- 22. J. L. J. Am. Chem. Soc. 116, 11622 (1994). ( , N. S. Mills, D. E. Kadlecek, J. A. Lowery. http://dx.doi.org/10.1021/ja00104a074)
- 23. E. Org. Synth. 54, 11 (1974). , W. Klug, A. Breuer.
- 24. G. A. J. Am. Chem. Soc. 102, 4485 (1980). ( , G. K. S. Prakash, G. Liang, P. W. Westerman, K. Kunde, J. Chandrasekhar, P. v. R. Schleyer. http://dx.doi.org/10.1021/ja00533a030)
- 25. C. J. Org. Chem. 76, 181 (2011). ( , J. Hatfield, S. Patel, D. Vasudevan, C. Tirla, N. S. Mills. http://dx.doi.org/10.1021/jo101871q)
- 26. N. S. J. Org. Chem. 70, 10709 (2005). ( , C. Tirla, M. A. Benish, A. J. Rakowitz, L. M. Bebell, C. M. M. Hurd, A. L. M. Bria. http://dx.doi.org/10.1021/jo051599u)
- 27. N. S. J. Org. Chem. 62, 9318 (1997). ( , J. L. Malandra, E. E. Burns, A. Green, K. E. Unruh, D. E. Kadlecek, J. A. Lowery. http://dx.doi.org/10.1021/jo971716o)
- 28. A. M. J. Am. Chem. Soc. 130, 14883 (2008). ( , N. S. Mills, A. Yousef. http://dx.doi.org/10.1021/ja8042323)
- 29. B. J. Org. Chem. 76, 5539 (2011). ( , M. Higbee, N. S. Mills. http://dx.doi.org/10.1021/jo200227t)
- 30. A. J. Am. Chem. Soc. 105, 2164 (1983). ( , A. Y. Meyer, R. Poupko, M. Rabinovitz. http://dx.doi.org/10.1021/ja00346a011)
- 31. A. Tetrahedron 41, 785 (1985). ( , A. Y. Meyer, M. Rabinovitz. http://dx.doi.org/10.1016/S0040-4020(01)96458-0)
- 32. N. S. J. Org. Chem. 69, 6623 (2004). ( , A. Levy, B. F. Plummer. http://dx.doi.org/10.1021/jo0499266)
- 33. Initial research on indenyldiene dications had revealed a tendency toward intramolecular cyclization, which could be avoided with a phenyl spacer to separate ring systems.
- 34. B. J. J. Am. Chem. Soc. 130, 10179 (2008). ( , N. S. Mills. http://dx.doi.org/10.1021/ja711501k)
- 35. B. J. Org. Lett. 10, 5605 (2008). ( , N. S. Mills. http://dx.doi.org/10.1021/ol802389n)
- 36. H. W. J. Am. Chem. Soc. 126, 8189 (2004). ( , C. E. Webster, L. M. Pérez, M. B. Hall, F. P. Gabbaï. http://dx.doi.org/10.1021/ja048501y)
- 37. S. P. J. Org. Chem. 76, 10254 (2011). ( , N. S. Mills. http://dx.doi.org/10.1021/jo201512n)
- 38. N. S. J. Org. Chem. 76, 645 (2011). ( , F. E. Cheng, J. M. Baylan, C. Tirla, J. L. Hartmann, K. C. Patel, B. J. Dahl, S. P. McClintock. http://dx.doi.org/10.1021/jo102220y)