A computational study of the mechanism of addition of singlet carbene analogues to 1,3-butadiene to form 1,1-dimethylmetallacyclopent-3enes [MMe 2C4H6, M = Si, Ge, Sn] and their reverse retro-addition reactions

Organometallics

Volumn 28, Issue 19, 2009, Pages 5612-5622

  Nag, Mrinmoy ^a   Gaspar, Peter P ^a  

^a WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRONIC STRUCTURE; ORGANIC COMPOUNDS;

1 ,3-BUTADIENE; 1 ,4-ADDITION; CARBENE ANALOGUES; COMPUTATIONAL STUDIES; DIMETHYLSILYLENE; ELECTRONIC STRUCTURE CALCULATIONS; REARRANGEMENT REACTIONS; STANNYLENES;

ADDITION REACTIONS;

EID: 70349767021     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om900369e     Document Type: Article

References (80)

1. (a) Becerra, R.; Walsh, R. Phys. Chem. Chem. Phys. 2007, 9, 2817.
2. (b) Tokitoh, N.; Ando, W In Reactive Intermediate Chemistry; Moss, R. A.; Platz, M., S.; Jones, M., Jr., Eds.; Wiley-Interscience: New York, 2004; pp 651-715.
3. (c) Gaspar, P. P.; West, R. In The Chemistry of Organic Silicon Compounds; Rappoport, Z.; Apeloig, Y., Eds.; John Wiley and Sons: New York, 1998; Vol. 2, pp 2463-2568.
4. (d) Becerra, R.; Walsh, R. Res. Chem. Kjpet. 1995, 3, 263-326.
5. (e) Weidenbruch, M. Coord. Chem. Rev. 1994, 130, 275.
6. (f) Gaspar, P. P. In Reactive Intermediates; Jones, M. Jr.; Moss, R. A., Eds.; John. Wiley and Sons: New York, 1985; Vol. 3, pp 333-427.
7. (g) Gaspar, P. P. In Reactive Intermediates, Jones, M., Jr.; Moss, R. A., Eds.; John Wiley and Sons: New York, 1981; Vol. 2, pp 335-385.
8. (h) Gaspar, P. P. In Reactive Intermediates; Jones, M., Jr.; Moss, R. A., Eds.; John Wiley and Sons: New York, 1978; Vol.1., pp 229-277.
9. (a) Boganov, S. E.; Egorov, M. P.; Faustov, V. I.; Krylova, I. V.; Nefedov, O. M.; Becerra, R.; Walsh, R. Russ. Chem. Bull., Int. Ed. 2005, 54, 483.
10. (b) Neumann, W. P. Chem. Rev. 1991, 91, 311.
11. (c) Becerra, R.; Boganov, S. E.; Egorov, M. P.; Lee, V. Y.; Nefedov, O. M.; Walsh, R. Chem. Phys. Lett. 1996, 250 (1), 111.
12. (d) Schriewer, M.; Neumann, W. P. Angew. Chem., Int. Ed. Engl. 1981, 20, 1019.
13. (e) Schriewer, M.; Neumann, W. P. J. Am. Chem. Soc. 1983, 105, 897.
14. (f) Neumann, W. P.; Michels, E.; Koecher, J. Tetrahedron Lett. 1987, 28, 3783.
15. (g) Lei, D.; Gaspar, P. P. Organometallics 1991, 10, 1221.
16. (h) Bobbitt, K. L.; Maloney, V. M.; Gaspar, P. P. Organometallics 1991, 10, 2772.
17. (i) Bobbitt, K. L.; Lei, D.; Maloney, V. M.; Parker, S. C.; Raible, J. M.; Gaspar, P. P. In Frontiers of Organogermanium, -Tin and -Lead Chemistry; Lukevics, E.; Ignatovich, L., Eds.; Latvian Institute of Organic Synthesis: Riga, 1993.
18. (a) Leigh, W. J.; Harrington, C. R.; Vargas-Baca, I. J. Am. Chem. Soc. 2004, 126 (49), 16105.
19. (b) Harrington, C. R.; Leigh, W. J.; Chan, B. K.; Gaspar, P. P.; Zhou, D. Can. J. Chem. 2005, 83, 1324.
20. (c) Leigh, W. J.; Lollmahomed, F.; Harrington, C. R. Organometallics 2006, 25, 2055.
21. (d) Leigh, W. J.; Lollmahomed, F.; Harrington, C. R; McDonald, J. M. Organometallics 2006, 25 (22), 5424.
22. (e) Huck, L. A.; Leigh, W. J. OreanoOrganometallics 2007, 26, 1339.
23. (f) Lollmahomed, F.; Huck, L. A.; Harrington, C. A.; Chitnis, S. S.; Leigh, W. Organometallics 2009, 28, 1484.
24. Davidson, P. J.; Harris, D. H.; Lappert, M. F. J. Chem. Soc, Dalton Trans. 1976, 21, 2268.
25. Becerra, R.; Gaspar, P. P.; Harrington, C. R.; Leigh, W. J.; Vargas-Baca, I.; Walsh, R.; Zhou, D. J. Am. Chem. Soc. 2005, 127, 17469.
26. Jones, M., Jr.; Moss, R. A. In Reactive Intermediate Chemistry; Moss, R. A., Platz, M. S., Jones, M., Jr., Eds.; Wiley-Interscience: Hoboken, NJ, 2004; pp 273-328.
27. Tomioka, H. In Reactive Intermediate Chemistry; Moss, R. A., Platz, M. S., Jones, M., Jr., Eds.; Wiley-Interscience: Hoboken, NJ, 2004; pp 375-461.
28. Doyle, M. P. In Reactive Intermediate Chemistry; Moss, R. A., Platz, M. S., Jones, M., Jr., Eds.; Wiley-Interscience: Hoboken, NJ, 2004; pp 561-592.
29. Ishikawa, M.; Kumada, M. J. Organomet. Chem. 1974, 81, C3.
30. Gaspar, P. P.; Xiao, M.; Pae, D. H.; Berger, D. J.; Haile, T.; Chen, T.; Lei, D.; Winchester, W. R.; Jiang, P. Organomet. Chem. 2002, 646, 68.
31. Hwang, R.-J.; Conlin, R. T.; Gaspar, P. P. J. Organomet. Chem. 1.975, 94, C38.
32. Ando, W.; Ohgaki, H.; Kabe, Y. Angew; Chem., Int. Ed. Engl. 1994, 33, 659.
33. Kabe, Y.; Ohgaki, H.; Yamagaki, T.; Nakanishi, H.; Ando, W. J. Organomet. Chem. 2001, 636, 82.
34. Frey, H. M. Tjyns. Faraday Soc. 1962, 58, 516.
35. Fujimoto, H.; Hoffmann, R. J. Phys. Chem. 1974, 78, 1167.
36. Zhang, S.; Conlin, R. T. J. Am. Chem. Soc. 1991, 113, 4272.
37. Moiseev, A. G.; Leigh, W. J. Organometallics 2007, 26, 6277.
38. Takeda, N.; Tokitoh, N.; Okazaki, R. Chem. Lett. 2000, 29, 622.
39. Atwell, W. H.; Weyenberg, D. H. J. Am. Chem. Soc. 1968, 90, 3438.
40. Ma, E. C.-L.; Kobayashi, K.; Barzilai, M. W.; Gaspar, P. P. J. Organomet. Chem. 1982, 224, C13.
41. Leigh, W. J.; Toltl, N. P.; Apodaca, P.; Castruita, M.; Pannell, K. H. Organometallics 2000, 19, 3232.
42. Zhou, D.; Reiche, C.; Nag, M.; Soderquist, J. A.; Gaspar, P. P. Organometallics 2009, 28, 2595.
43. Zhou, D. Doctoral Dissertation, Washington University, 2004.
44. Cotton, J. D.; Davidson, P. J.; Lappert, M. F. J. Chem. Soc, Dalton Trans. 1976, 2275.
45. Marx, R.; Neumann, W. P.; Hillner, K. Tetrahedron Lett. 1984, 25, 625.
46. Kami, M.; Kapp, J.; Schleyer, P. v. R.; Apeloig, Y. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; John Wiley and Sons: Chichester, 2001; Vol. 3, pp 1-164.
47. Gordon, M. S.; Nelson, W. Organometallics 1995, 14, 1067.
48. Sakai, S. M. J. Quantum Chem. 1997, 70, 291.
49. Su, M.-D., Chu, S.-Y. J. Am. Chem. Soc. 1999, 121, 11478.
50. Su, M.-D. Chem.-Eur. J. 2004, 10, 6073.
51. Chung, G.; Gordon, M. S. Organometallics 1999,18 4881.
52. Dewar, M. J. S.; Friedheim, J. E.; Grady, G. L. Organometallics 1985, 4, 1784.
53. Hehre, W. J.; Kong, J. Spartan '04 Windows; Wavefunction Inc.: Irvine, CA, 2004.
54. Raghavachari, K.; Trucks, G. W.; Pople, J. A.; Head-Gordon, M. Chem. Phys. Lett. 1989, 157,479.
55. 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.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, M.; Cossi, M.; Scalmani, G.; Rega, N.; Peterssom, G. A.; Nakatsuji, M.; Hoda, 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.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, 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 C.02-E.01; Gaussian Inc.: Wallingford, CT 2004.
56. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
57. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623.
58. Hay, P. J.; Wadt, W., R. J. Chem. Phys. 1985, 82, 270.
59. Hay, P. J.; Wadt, W., R. J. Chem. Phys. 1985, 82, 284.
60. Hay, P. J.; Wadt, W., R. Chem. Phys. Lett. 1985, 82, 299.
61. Dunning, T. H., Jr. J. Chem. Phys. 1989, 90, 1007.
62. Woon, T. E.; Dunning, T. H., Jr. J. Chem. Phys. 1993, 98,1358.
63. Peterson, K., A. -J. Chem. Phys. 2003, 119, 11099.
64. Peterson, K., A.; J. Chem. Phys. 2003, 119, 11113.
65. Lynch, B. J.; Fast, P. L.; Harris, M.; Truhlar, D. G. J. Phys. Chem. A 2000, 104, 4811.
66. Lynch, B. J.; Truhlař, D. G. J. Phys. Chem. A 2001, 105, 2936.
67. http://comp.chem.umn.edu/database/freq-scale.htm.
68. http://comp.chem.umn.edu/basissets/basis.cgi.
69. Apeloig, Y.; Sklenak, S. Can; J. Chem. 2000, 78, 1496.
70. Su, M.-D.; Chu, S.-Y. Phys. Chem. A 1999, 103, 11011.
71. Barthelat, J.-C.; Roch, B. S.; Trinquier, G.; Satge, J. J. Am. Chem. Soc. 1980, 102, 4080.
72. Aston, J. G.; Szasz, H. W.; W,W. H.; Brickwedde, F. G. J. Chem. Phys. 1946, 14, 67.
73. Lei, D.; Gaspar, P. P. Res. Chem. Intermed. 1989, 12, 103.
74. Lei, D.; Gaspar, P. P. Organometallics 1985, 4, 1471.
75. Lei, D.; Hwang, R. J.; Gaspar, P. P. J. Organomet. Chem. 1984, 271, 1.
76. Houk, K. N.; Rondan, N. G.; Mareda, J. Tetrahedron 1985, 41, 1555.
77. Baggott, J. E.; Blitz, M. A.; Frey, H. M.; Lightfoot, P. D.; Walsh, R. J. Chem. Soc., Faraday Trans. 2 1988, 84, 515.
78. Moiseev, A. G.; Leigh, W. J. Organometallics 2007, 26, 6268.
79. Bobbitt, K. L.; Gaspar, P. P. J. Oganomet. Chem. 1995, 499, 17.
80. Leigh, W. J.; Harrington, C. R. J. Am. Chem. Soc. 2005, 127, 5084.