128
Views
3
CrossRef citations to date
0
Altmetric
Original Articles

Aromaticity of 1,4-dehydrotropylium ion and its mono- and poly-phospha analogues

, , &
Pages 674-682 | Received 27 Nov 2016, Accepted 29 Dec 2016, Published online: 25 May 2017

References

  • Wittig, G. Angew. Chem. Int. Ed. 1965, 4, 729-797.
  • Kauffmann, T.; Boettcher, F-P. Chem. Ber. 1962, 95, 949-955.
  • Im, G-Y. J.; Bronner, S. M.; Goetz, A. E.; Paton, R. S.; Cheong, P. H.-Y.; Houk, K. N.; Garg, N. K. J. Am. Chem. Soc. 2010, 132, 17933-17944.
  • Kauffmann, T. Angew. Chem. Int. Ed. 1965, 4, 543-557.
  • Sondheimer, F. Acc. Chem. Res. 1972, 5, 81-91.
  • Gellini, C.; Salvi, P. R. Symmetry 2010, 2, 1846-1924.
  • Spitler, E. L.; Johnson II, C. A.; Haley, M. M. Chem. Rev. 2006, 106, 5344-5386.
  • Cresp, T. M.; Sondheimer, F. Tetrahedron Lett. 1982, 23, 1731-1734.
  • Stockel, K.; Sondheimer, F. Org. Synth. 1974, 54, 1-1.
  • Januar, L. A.; Huynh, V.; Wood, T. S.; Castro, C.; Karney, W. L. J. Org. Chem. 2011, 76, 403-407.
  • ( a) Amiralaei, S.; Gauld, J.; Green, J. R. Chem. Eur. J. 2011, 17, 4157-4165, ( b) Klosin, J.; Abboud, K. A.; Jones, W. M. Organometallics 1996, 15, 596-603, ( c) Klosen, J.; Abboud, K. A.; Jones, W. M. Organomettalics 1996, 15, 2465-2468, ( d) Klosen, J.; Abboud, K. A.; Jones, W. M. Organometallics 1995, 14, 2892-2902, ( e) Lu, Z.; Jones, W. M. Organometallics 1994, 13, 1539-1541, ( f) Lu, Z.; Abboud, K. A.; Jones, W. M. J. Am. Chem. Soc. 1992, 114, 10991-10992.
  • Iwasawa, N.; Satoh, H. J. Am. Chem. Soc. 1999, 121, 7951-7952.
  • Juselius, J.; Sundholm, D. Phys. Chem. Chem. Phys. 2001, 3, 2433-2437.
  • Hoffmann, R.; Imamura, A.; Hehre, W. J. J. Am. Chem. Soc. 1968, 90, 1499-1509.
  • Kraka, E.; Cremer, D. J. Am. Chem. Soc. 1994, 116, 4929-4936.
  • Yavari, I.; Norouzi-Arasi, H. J. Mol. Struct: THEOCHEM 2002, 593, 199-207.
  • Anand, S.; Schlegel, H. B. Mol. Phys. 2006, 104, 933-941.
  • Zou, C.; Lepetit, C.; Coppet, Y.; Chauvin, R. Pure. Appl. Chem. 2006, 78, 791-811, and references cited therein.
  • ( a) Doering, W. v. E.; Krauch, H. Angew.Chem. 1956, 68, 661-667, ( b) Lifshitz, C. Acc. Chem. Res. 1994, 27, 138-144. ( c) Nicolaides, A.; Radom, L. J. Am. Chem. Soc. 1996, 118, 10561-10570, ( d) Fridgen, T. D.; Troe, J.; Viggiano, A. A.; Priday, A. J.; Williams, S.; McMahon, T. B, J. Phys. Chem. A. 2004, 108, 5600-5609, ( e) Ghiasi, R. Main Group Chemistry 2008, 7, 147-154, ( f) Bullins, K. W.; Huang, T. T. S.; Kirkby, S. J. Int. J. Quant. Chem. 2009, 109, 1322-1327, ( g) Komatsu, K. Chem. Rec. 2015, 15, 160-174.
  • Lin, L.; Lievens, P.; Nguyen, M. T. J. Mol. Struct. 2010, 943, 23-31.
  • Firouzi, R.; Ardoni, S. S. Phys. Chem. Chem. Phys. 2014, 16, 11538-11548.
  • Puri, A.; Gupta, R. Molecules 2016, 21, 1099.
  • Bergman, R. G.; D'Amore, M. B. J. Am. Chem. Soc. 1969, 91, 5694-5695.
  • D'Amore, M. B.; Bergman, R. G.; Kent, M.; Hedaya, E. J. Chem. Soc. Chem. Commun. 1972, 49-50.
  • Saini, P.; Bhasin, P.; Bansal, R. K. Comp. Theo. Chem. 2013, 1017, 72-77.
  • Appel, R. Pure App. Chem. 1987, 59, 977-982.
  • Nyulászi, L.; Varnai, P.; Krill, S.; Regitz, M. J. Chem. Soc. Perkin Trans. 1995, 2, 315-318.
  • Cloke, F. G. N.; Hitchcock, P. B.; Nixon, J. F.; Wilson, D. J.; Tabellion, F.; Fischbeck, U.; Preuss, F.; Regitz, M. Chem. Commun. 1999, 2363-2364.
  • Simpson, M. C.; Protasiewicz, J. D. Pure App. Chem. 2013, 85, 801-815.
  • Gupta, R.; Maheshwari, P.; Kour, M. Comp. Theo. Chem. 2015, 1060, 10-16.
  • Padma Malar, E. J. J. Org. Chem. 1992, 57, 3694-3698.
  • Gupta, R.; Bansal, R. K. Comp. Theo. Chem. 2016, 1076, 1-10.
  • Dillon, K. B.; Mathey, F.; Nixon, J. F. Phosphorus: The Carbon Copy: From Organophosphorus to Phospha-organic Chemistry, 1998, Wiley: New York.
  • Krygowski, T. M.; Szatylowicz, H.; Stasyuk, O. A.; Dominikowska, J.; Palusiak, M. Chem. Rev. 2014, 114, 6383-6422.
  • Julg, A.; Francois, P. Theo. Chim. Acta 1967, 8, 249-259.
  • ( a) Bird, C. W. Tetrahedron 1985, 41, 1409-1414, ( b) Bird, C. W. Tetrahedron 1986, 42, 89-92, ( c) Bird, C. W. Tetrahedron 1987, 43, 4725-4730, ( d) Bird, C. W. Tetrahedron 1990, 46, 5697-5702, ( e) Bird, C. W. Tetrahedron 1992, 48, 335-340.
  • Schleyer, P. v. R.; Puhlhofer, F. Org. Lett. 2002, 4, 2873-2876.
  • Pascal, P. Ann. Chim. Phys. 1910, 19, 5-70.
  • Mitchell, R. H. Chem. Rev. 2001, 101, 1301-1315.
  • ( a) Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; Hommes, N. J. R. V. E. J. Am. Chem. Soc. 1996, 118, 6317-6318, ( b) Schleyer, P. v. R.; Jiao, H. J.; Hommes, N. J. R. V. E.; Malkin, V. G.; Malkina, O. L. J.Am.Chem.Soc. 1997, 119, 12669-12670.
  • Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; lyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R.; Yazyev, O.; Auatin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A.; Gaussian 03, Revision B.05; Gaussian, Inc: Wallingford, CT, 2003.
  • Bader, R. F. W. Atoms in Molecules - A Quantum Theory, 1990, Clarendon Press: Oxford.
  • AIMP Program Package. http://www.chemistry.mcmaster.ca/aimpac/imagemap/imagemap.htm>
  • Nyulászi, L. Chem. Rev. 2001, 101, 1229-1246.
  • Nyulászi, L.; Benko, Z. Aromatic Phosphorus Heterocycles In Aromaticity in Heterocyclic Compounds, Krygowski, T. M.; Cyranski, M. K.; Eds. 2009 Springer-Verlag: Berlin/Heidelberg, 19, 27-81.
  • Nyulászi, L. Tetrahedron 2000, 56, 79-84.
  • Reed, A. E.; Weinhold, F. J. Chem. Phys. 1985, 83, 1736-1740.
  • Pearson, R. G. Proc. Natl. Acad. Sci : USA 1986, 83, 8440-8441.
  • Haddon, R. C.; Fukunga, T. Tetrahedron Lett. 1980, 21, 1191-1192.
  • Zhou, Z.; Parr, R. G. Tetrahedron Lett. 1988, 29, 4843-4846.
  • Wheeler, S. E.; Houk, K. N.; Schleyer, P. v. R.; Allen, W. D. J. Am. Chem. Soc. 2009, 131, 2547-2560.
  • Dransfeld, A.; Nyulászi, L.; Schleyer, P. v. R. Inorg. Chem. 1998, 37, 4413-4420.
  • Hine, J.; Knight, D. B. J. Org. Chem. 1970, 35, 3946-3949.
  • Chen, Z.; Wannere, C. S.; Corminboeuf, C.; Puchta, R.; Schleyer, P. v. R. Chem. Rev. 2005, 105, 3842-3888.
  • Steiner, E.; Fowler, P. W.; Jennesken, L. W. Angew. Chem. Int. Ed. 2001, 40, 362-366.
  • Dauben, H. J.; Ir. Wilson, J. D.; Laity, J. L. In Diamagnetic susceptibility exaltation as criterion of aromaticity in nonbenzenoid aromatics, Synder, J. P. ( ed.) 1971, Academic Press: New York, 2, 167-206.
  • Schleyer, P. v. R.; Freeman, P. K.; Jiao, H.; Goldfuss, B. Angew. Chem. Int. Ed. Engl. 1995, 34, 337-340.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.