Density Functional Theory Study on Dimerizations of Phospholes

Organometallics

Volumn 22, Issue 26, 2003, Pages 5526-5533

  Dinadayalane, T C ^a   Sastry, G Narahari ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

OLIGOMERIZATION; TRANSITION STATES;

ACTIVATION ENERGY; ADDITION REACTIONS; CHEMICAL BONDS; COMPUTATIONAL METHODS; DIMERIZATION; DIMERS; ENTHALPY; GIBBS FREE ENERGY; POLYMERIZATION; PROBABILITY DENSITY FUNCTION; REACTION KINETICS;

ORGANOMETALLICS;

EID: 0346937515     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0340490     Document Type: Article

References (60)

1. Mathey, F. Chem. Rev. 1988, 88, 429.
2. Bird, C. W. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, U.K., 1996; Vol. 2.
3. (a) Leavitt, F. C.; Manuel, T. A.; Johnson, F. J. Am. Chem. Soc. 1959, 81, 3163.
4. (b) Quin, L. D.; Bryson, J. G. J. Am. Chem. Soc. 1987, 89, 5984.
5. Charrier, C.; Bonnard, H.; de Lauzon, G.; Mathey, F. J. Am, Chem. Soc. 1988, 105, 6871.
6. (a) Mattmann, E.; Simonutti, D.; Ricard, L.; Mercier, F.; Mathey, F. J. Org. Chem. 2001, 66, 755.
7. (b) Mattmann, E.; Mathey, F.; Sevin, A.; Frison, G. J. Org. Chem. 2002, 67, 1208.
8. Nyulaszi, L. Chem. Rev. 2001, 101, 1229.
9. (a) Mathey, F.; Mercier, F.; Charrier, C.; Fischer, J.; Mitschler, A. J. Am. Chem. Soc. 1981, 103, 4595.
10. (b) Charrier, C.; Bonnard, H.; Mathey, F. J. Org. Chem. 1982, 47, 2376.
11. de Lauzon, G.; Charrier, C.; Bonnard, H.; Mathey, F.; Fischer, J.; Mitschler, A. J. Chem. Soc., Chem. Commun. 1982, 1272.
12. (a) Mathey, F.; Mercier, F. C. R. Acad. Sci. Paris, Ser. IIb 1997, 324, 701.
13. (b) Laporte, F.; Mercier, F.; Ricard, L.; Mathey, F. Bull. Soc. Chim. Fr. 1993, 130, 843.
14. (c) Le Goff, P.; Mathey, F.; Ricard, L. J. Org. Chem. 1989, 54, 4754.
15. Dinadayalane, T. C.; Geetha, K.; Sastry, G. N. J. Phys. Chem. A 2003, 707, 5479.
16. (a) Geetha, K.; Dinadayalane, T. C.; Sastry, G. N. J. Phys. Org. Chem. 2003, 16, 298.
17. (b) Geetha, K.; Sastry, G. N. Ind. J. Chem. A 2003, 42A, 11.
18. (a) Dinadayalane, T. C.; Vijaya, R.; Smitha, A.; Sastry, G. N. J. Phys. Chem. A 2002, 106, 1627.
19. (b) Vijaya R.; Dinadayalane T.C.; Sastry G.N. J. Mol. Struct. (THEOCHEM) 2002, 589-590, 291
20. (a) Dinadayalane, T. C.; Sastry, G. N. J. Chem. Soc., Perkin Trans. 2 2002, 1902.
21. (b) Dinadayalane, T. C.; Punnagai, M.; Sastry, G. N. J. Mol. Struct. (THEOCHEM) 2003, 626, 247.
22. Bachrach, S. M.; Perriott, L. J. Org. Chem. 1994, 59, 3394.
23. (a) Bachrach, S. M. J. Org. Chem. 1994, 59, 5027.
24. (b) Salzner, U.; Bachrach, S. M. J. Organomet. Chem. 1997, 529, 15
25. Bachrach, S. M.; Perriott, L. M. Can. J. Chem. 1998, 74, 839.
26. Keglevich, G.; Nyulaszi, L.; Chuluunbaatar, T.; Namkhainyambuu, B.-A.; Ludanyi, K.; Imre, T.; Toke, L. Tetrahedron 2002, 58, 9801.
27. Aitken, R. A.; Claaper, P. N.; Wilson, N. J. Tetrahedron Lett. 1999, 40, 5271.
28. Vlaar, M. J. M.; de Kanter, F. J. J.; Schakel, M.; Lutz, M.; Spek, A. L. ; Lammertsma, K. J. Organomet. Chem. 2001, 617-618, 811.
29. Keglevich, G.; Kegl, T.; Chuluunbaatar, T.; Dajka, B.; Matyus, P.; Balogh, B.; Kollar, L. J. Mol. Catal A 2003, 200, 181.
30. (a) Mathey, F. J. Organomet. Chem. 2002, 646, 15.
31. (b) Janiak, C.; Versteeg, U.; Lange, K. C. H.; Weimann, R.; Hahn, E. J. Organomet. Chem. 1995, 501, 219.
32. (c) de Boer, E. J. M.; Gihnore, I. J.; Korndorffer, F. M.; Horton, A. D. ; van der Linden, A.; Royan, B. W.; Ruisch, B. J.; Schoon, L.; Shaw, R. W. J. Mol. Catal. A 1996, 128, 155.
33. (d) Brown, S. J.; Gao, X.; Harrison, D. G.; Koch, L.; Spence, R. E. v. H.; Yap, G. P. A. Organometallics 1998, 17, 5445.
34. (e) Salzner, U.; Lagowski, J. B.; Pickup, P. G.; Poirier, R. A. Synth. Met. 1998, 96, 177.
35. (a) Mathey, F.; Mercier, F.; Robin, F.; Ricard, L. J. Organomet, Chem. 1998, 577, 117.
36. (b) Wilkes, L. M.; Nelson, J. H.; McCusker, L. B.; Seff, K.; Mathey, F. Inorg. Chem. 1988, 22, 2476.
37. (c) Choudary, B. M.; Reddy, N. P.; Jamil, M. Z. Polyhedron 1986, 5, 911.
38. (d) Loh, S.-K.; Vittal, J. J.; Leung, P.-H. Tetrahedron: Asymmetry 1998, 9, 423.
39. de Lauzon, G.; Charrier, C.; Bonnard, H.; Mathey, F. Tetrahedron Lett. 1982, 23, 511.
40. Delaere, D.; Nguyen, M. T.; Vanquickenborne, L. G. J. Organomet. Chem. 2002, 643-644, 194.
41. Keseru, G. M.; Keglevich, G. J. Organomet. Chem. 1999, 556, 166.
42. Marchand, A. P.; Ganguly, B.; Malagon, C. I.; Lai, H.; Watson, W. H. Tetrahedron 2003, 59, 1763.
43. (a) Keglevich, G.; Chuluunbaatar, T.; Ludanyi, K.; Toke, L. Tetrahedron 2000, 56, 1.
44. (b) Quin, L. D.; Mesch, K. A. J. Chem. Soc., Chem. Commun. 1980, 959.
45. (c) Mathey, F.; Mercier, F. Tetrahedron Lett. 1981, 22, 319.
46. (a) Caramella, P.; Qadrelli, P.; Tomo, L. J. Am. Chem. Soc. 2002, 124, 1130.
47. (b) Qadrelli, P.; Romano, S.; Toma, L.; Caramella, P. J. Org. Chem. 2003, 68, 6035.
48. Tomioka, H.; Hirano, Y.; Izawa, Y. Tetrahedron Lett. 1974, 15, 4477.
49. (a) Goldstein, E.; Beno, B.; Houk, K. N. J. Am. Chem. Soc. 1996, 118, 6036.
50. (b) Beno, B. R.; Wilsey, S.; Houk, K. N. J. Am. Chem. Soc. 1999, 121, 4816.
51. (c) Jursic, B.; Zdravkovski, Z. J. Chem. Soc., Perkin Trans. 2 1995, 1223.
52. (d) Jorgensen, W. L.; Lim, D.; Blake, J. F. J. Am. Chem. Soc. 1993, 11B, 2936.
53. Bally, T.; Albrecht, B.; Matzinger, S.; Sastry, G. M. MOPLOT 3.2; University of Fribourg, 1997.
54. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; 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.; Gui, Q.; Morokuma, K.; Rega, N.; Salvador, P.; Dannenberg, J. J.; 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, F.; Komaromi, I.; Gomperts, R.; 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. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A.; Gaussian 98, Revision A.11.2; Gaussian, Inc., Pittsburgh, FA, 2001.
55. Several attempts made to locate the transition state 3P-TS-endo3 at the B3LYP level were in vain, Only the PM3 level of theory facilitated location of the correct transition-state structure which was used for single-point calculations.
56. (a) Salem, L. J. Am. Chem. Soc. 1968, 90, 553.
57. (b) Birney, D. M.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 4127.
58. Benford, G. A.; Wassermann, A. J. Chem. Soc. 1939, 362.
59. Mehta, G.; Padma, S.; Jemmis, E. D.; Leela, G.; Osawa, E.; Barbiric, D. A. Tetrahedron Lett. 1988, 29, 1613.
60. Mehta, G.; Viswanath, M. B.; Sastry, G. N.; Jemmis, E. D.; Reddy, D. S. K.; Kunwar, A. C. Angew. Chem., Int. Ed. Engl. 1993, 31, 1488.