Computational assessment of 1,3-dipolar cycloaddition of nitrile oxides with ethene and [60]fullerene

Heterocycles

Volumn 84, Issue 2, 2012, Pages 719-735

  Rhyman, Lydia ^a   Jhaumeer Laulloo, Sabina ^a   Domingo, Luis R ^b   Joule, John A ^c   Ramasamia, Ponnadurai ^a  

^a UNIVERSITY OF MAURITIUS   (Mauritius)

^b UNIVERSITY OF VALENCIA   (Spain)

^c UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84856537864     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-11-S(P)46     Document Type: Article

References (79)

1. H. W. Kroto, J. R. Heath, S. C. O'Brien, R. F. Curl, and R. E. Smalley, Nature, 1985, 318, 162.
2. W. Krätshmet, L. D. Lamb, K. Fostiropoulos, and D. R. Huffman, Nature, 1990, 347, 354.
3. M. A. Yurovskaya and I. V. Trushkov, Russ. Chem. Bull. Int. Ed., 2002, 51, 367.
4. X. Lu and Z. F. Chen, Chem. Rev., 2005, 105, 3643
5. H. Sun, X. Yun, S. Wu, and Q. Teng, J. Mol. Struct. (THEOCHEM), 2008, 868, 71
6. Z. F. Chen and R. B. King, Chem. Rev., 2005, 105, 3613
7. M. H. O. Rashid, C. Lim, and C. H. Choi, Bull. Korean Chem. Soc., 2010, 31, 1681.
8. L. B. Piotrovskii, Ros. Nanotekhnol., 2007, 2, 6
9. R. Bakry, R. M. Vallant, M. Najam-ul-Haq, M. Rainer, Z. Szabo, C. W Huck, and G. K. Bonn., Int. J. Nanomed., 2007, 2, 639
10. Z. Markovic and V. Trajkovic, Biomaterials, 2008, 29, 3561.
11. M. Prato and M. Maggini, Acc. Chem. Res., 1998, 31, 519
12. M. Prato, Top. Curr. Chem., 1999,199, 173
13. F. Diederich and M. Gómez-López, Chem. Soc. Rev., 1999, 28, 263
14. D. M. Guldi, F.Zerbetto, V. Georgakilas, and M. Prato, Acc. Chem. Res., 2005, 38, 38.
15. E. Nakamura and H. Isobe, Acc. Chem. Res., 2003, 36, 807
16. E. Nakamura and H. Isobe, Chem. Rec., 2010, 10, 260
17. R. Maeda-Mamiya, E. Noiri, H. Isobe, W. Nakanishi, K. Okamoto, K. Doi, T. Sugaya, T. Izumi, T. Homma, and E. Nakamura, Proc. Natl. Acad. Sci., 2010, 107, 5339.
18. Z. Xiao, F. Wang, S. Huang, L. Gan, J. Zhou, G. Yuan, M. Lu, and J. Pan, J. Org. Chem., 2005, 70,2060
19. N. Martín, M. Altable, S. Filippone, A. Martín-Domenech, M. Güelle, and M. Solà, Angew.Chem. Int. Ed., 2006, 45, 1439
20. N. Masakazu, Y. Segawa, and K. Itami, J. Am. Chem. Soc., 2011, 133, 2402.
21. I. Y. Podolski, Z. A. Podlubnaya, and O. V. Godukhin, Biophysics, 2010, 55, 71.
22. A. Hirsch and M. Brettreich, Fullerenes: Chemistry and Reactions, Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KgaA, 2005.
23. A. Hirsch, Synthesis, 1995, 895
24. W. Silwa, Fullerene Sci. Technol., 1995, 3, 243
25. M. A.Yurovskaya, and A. A. Ovcharenko, Khim. Geterotsikl Soedin., 1998, 291
26. [Chem. Heterocycl. Compd.,1998 (Engl. Transl.)]
27. E. N. Karaulova and E. I. Baggi, Usp. Khim., 1999, 68, 979.
28. [Russ. Chem. Rev., 1999, 68 (Engl. Transl.)].
29. M. Maggini, G. Scorrano, and M. Prato, J. Am. Chem. Soc., 1993, 115, 9798
30. M. Prato and M.Maggini, Acc. Chem. Res., 1998, 31, 519
31. M. Holzinger, O. Vostrowsky, A. Hirsh, F. Hennrich, M. Kappes, R. Weiss, and F. Jellen, Angew. Chem., 2001, 113, 4132
32. [Angew. Chem. Int. Ed., 2001, 40, 4002]
33. N. Tagmatarchis and M. Prato, J. Mater. Chem., 2004, 14, 437
34. S. Filipponne, M. I.Baraso, A. Martín-Domenech, S. Osuna, M. Solà, and N. Martín, Chem. Eur. J., 2008, 14, 5198.
35. T. Suzuki, Q. Li, K. C. Khemani, and F. Wudl, J. Am. Chem. Soc., 1992, 114, 7301.
36. A. Hirsch and M. Brettreich, Fullerenes: Chemistry and Reactions, Wiley-VCHVerlag GmbH & Co., KGaA, 2005
37. F. Langa and J.-F. Nierengarten, Fullerenes: Principles and Applications, RSC Publishing, 2007.
38. For some recent papers see: (a) F. Liu, W. Du, Q. Liang, Y. Wang, J. Zhang, J. Zhao, and S. Zhu,Tetrahedron, 2010, 66, 5467
39. H. Kitamura, K. Kokubo, and T. Oshima, Org. Lett., 2007, 9, 4045
40. V. A. Ioutsi, A. A. Zadorin, P. A. Khavrel, N. M. Belov, N. S. Ovchinnikova, A. A. Goryunkov, O. N. Kharybin, E. N. Nikolaev, M. A. Yurovskaya, and L. N. Sidorov, Tetrahedron, 2010, 66, 3037
41. G.-W. Wang, H.-T. Yang, P. Wu, C.-B. Miao, and Y. Xu, J. Org. Chem., 2006, 71, 4346
42. G.-W.Wang and H.-T. Yang, Tetrahedron Lett., 2007, 48, 4635.
43. H.-T. Yang, X.-J. Ruan, C.-B. Miao, and X.-Q. Sun, Tetrahedron Lett., 2010, 51, 6056.
44. M. S. Meier and M. Poplawska, J. Org. Chem., 1993, 58, 4524
45. M. S. Meier, D. J. Rice, C.Thomas, V. Majidi, R. Pogue, and M. Poplawska, Mat. Res. Soc. Symp. Proc., 1995, 359, 369
46. H.Irngartinger, C. M. Höhler, U. Huber-Patz, and W. Krätshmer, Chem. Ber., 1994, 127, 581
47. M.Aulbach, and H. U. Ter Meer (Hoechst AG), DE 4240042, 1994
48. [Chem. Abstr., 1995, 122, 31507n]
49. H. Irngartinger, A. Weber, and T. Escher, Liebigs Ann., 1996, 1845
50. T. Da Ros, M. Prato, F. Novello,M. Maggini, M. De Amici, and C. De Micheli, Chem. Commun., 1997, 59
51. K. Kavitha and P. Venuvanalingam, J. Org. Chem., 2005, 70, 5426.
52. http://pages.unibas.ch/mdpi/ecsoc/e0002/calelecg.htm.
53. H. Stolzenberg, B. Weinberger, W. P. Fehlhammer, F. G. Pühlhofer, and R. Weiss, Eur. J. Inorg. Chem., 2005, 4263.
54. H. Wang, Y. Wang, K. Han, and X. Peng, J. Org. Chem., 2005, 70, 4910.
55. K. B. Wiberg, Tetrahedron, 1968, 24, 1083.
56. L. R. Domingo, M. T. Picher, P. Arroyo, and J. A. Saez, J. Org. Chem., 2006, 71, 9319
57. L. R. Domingo, M. J. Aurell, P. Pérez, and R. Contreras, Tetrahedron, 2002, 58, 4417
58. P.Pérez, L. R. Domingo, M. J. Aurell, and R. Contreras, Tetrahedron, 2003, 59, 3117
59. P. Pérez, L.R. Domingo, A. Aizman, and R. Contreras, In Theoretical Aspects of Chemical Reactivity: ed. by A. Toro-Labbé; Elsevier Science: Amsterdam, the Netherlands, 2007; Vol. 19, pp. 139-201.
60. P. Jaramillo, L. R. Domingo, E. Chamorro, and P. Pérez, J. Mol. Struct.: (Theochem), 2008, 865, 68.
61. L. R. Domingo and J. A. Saez, J. Org. Chem., 2011, 76, 373.
62. A. D. Becke, J. Chem. Phys., 1988, 38, 3098.
63. C. Lee, W. Yang, and R. G. Parr, Phys. Rev. B, 1988, 37, 785.
64. W. J. Hehre, L. Radom, P. v. R. Schleyer, and J. A. Pople, Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
65. CYLview, 1.0b; C. Y. Legault, Université de Sherbrooke, 2009 (http://www.cylview.org).
66. C. Gonzalez and H. B. Schlegel, J. Chem. Phys., 1989, 90, 2154
67. C. Gonzalez and H. B. Schlegel, J. Phys. Chem., 1990, 94, 5523.
68. A. E. Reed, R. B. Weinstock, and F. Weinhold, J. Chem. Phys., 1985, 83, 735
69. A. E. Reed, L. A. Curtiss, and F. Weinhold, Chem. Rev., 1988, 88, 899.
70. R. G. Parr, L. von Szentpaly, and S. Liu, J. Am. Chem. Soc., 1999, 121, 1922.
71. R. G. Parr and R. G. Pearson, J. Am. Chem. Soc. 1983, 105, 7512
72. R. G. Parr and W. Yang, Density Functional Theory of Atoms and Molecules, Oxford University Press, New York, 1989.
73. W. Kohn and L. Sham, J. Phys. Rev. A, 1965, 140, 1133.
74. L. R. Domingo, E. Chamorro, and P. Pérez, J. Phys. Chem. A, 2008, 112, 4615.
75. D. G. Truhlar, A. D. Issacson, and B. C. Garett, In Generalized Transition State Theory, Vol 4 of Theory of Chemical Reaction Dynamics, pp. 65-137, CRC Press, Boca Raton, FL, 1985
76. M. J. Pilling and P. W. Seakins, In Reaction Kinetics, 2nd ed, Oxford Science, Oxford, 1995
77. P. R. P. Barreto, A. F. A. Vilela, and R. Gargano, Int. J. Quantum Chem., 2005, 103, 685.
78. E. P. Z. Wigner, Phys. Chem. B, 1932, 19, 203.
79. Supplementary materials are available with the authors upon request.