A theoretical study of mechanisms of 1,3-silyl migration in formylmethylsilane and related migrations. Comparison with allylsilane

Journal of the American Chemical Society

Volumn 121, Issue 37, 1999, Pages 8597-8603

  Takahashi, Masae ^a   Kira, Mitsuo ^a,b  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; GERMANIUM; SILANE; SILANE DERIVATIVE; SILICONE; TIN;

ARTICLE; CHEMICAL STRUCTURE; ISOMERISM; MOLECULAR DYNAMICS; PHYSICAL CHEMISTRY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033595558     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9911263     Document Type: Article

References (44)

1. Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry; Academic Press: New York, 1970.
2. Boyd, S. L.; Boyd, R. J.; Shi, Z.; Barclay, L. R. C.; Porter, N. A. J. Am. Chem. Soc. 1993, 115, 687.
3. (a) Berson, J. A.; Nelson, G. L. J. Am. Chem. Soc. 1967, 89, 5503.
4. (b) Berson, J. A.; Nelson, G. L. J. Am. Chem. Soc. 1970, 92, 1096.
5. (c) Berson, J. A.; Salem, L. J. Am. Chem. Soc. 1972, 94, 8917.
6. (d) Berson, J. A. Acc. Chem. Res. 1972, 5, 406.
7. (a) Baldwin, J. E.; Belfield, K. D. J. Am. Chem. Soc. 1988, 110, 296.
8. (b) Klärner, F.-G.; Drewes, R.; Hasselmann, D. J. Am. Chem. Soc. 1988, 110, 297.
9. For reviews, see: (a) Brook, A. G. Acc. Chem. Res.1974, 7, 77. (b) Brook, A. G.; Bassindale, A. R. Rearrangements in Ground and Excited States; de Mayo, P. Ed.; Academic Press: London, 1980; Vol. 2, Essay 9.
10. For reviews, see: (a) Brook, A. G. Acc. Chem. Res.1974, 7, 77. (b) Brook, A. G.; Bassindale, A. R. Rearrangements in Ground and Excited States; de Mayo, P. Ed.; Academic Press: London, 1980; Vol. 2, Essay 9.
11. (a) Kwart, H.; Slutsky, J. J. Am. Chem. Soc. 1972, 94, 2515.
12. (b) Slutsky, J.; Kwart, H. J. Am. Chem. Soc. 1973, 95, 8678.
13. Brook, A. G.; MacRae, D. M.; Limburg, W. W. J. Am. Chem. Soc. 1967, 89, 5493.
14. Takahashi, M.; Kira, M. J. Am. Chem. Soc. 1997, 119, 1948.
15. Yamabe, T.; Nakamura, K.; Shiota, Y.; Yoshizawa, K.; Kawauchi, S.; Ishikawa, M. J. Am. Chem. Soc. 1997, 119, 807.
16. Zhang, L. C.; Kabuto, C.; Kira, M. J. Am. Chem. Soc. 1999, 121, 2925.
17. (a) Brook, A. G.; MacRae, D. M.; Bassindale, A. R. J. Organomet. Chem. 1975, 86, 185.
18. (b) Larson, G. L.; Fernandez, Y. V. J. Organomet. Chem. 1975, 86, 193.
19. Kwart, H.; Barnette, W. E. J. Am. Chem. Soc. 1977, 99, 614.
20. Frish, M. J.; Truck, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Repolgle, E. S.; Gompers, M.; Andrews, J. A.; Ragchavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, J.; Baker, J.; Stewart, J. P.; Pople, J. A. GAUSSIAN 94, Gaussian Inc.: Pittsburgh, PA, 1994.
21. (a) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270.
22. (b) Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284.
23. (c) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
24. (a) Bader, R. F. W. Atoms in Molecules. A Quantum Theory.; Oxford University Press: Oxford, 1990.
25. (b) Kraka, E.; Cremer, D. Chemical Implication of Local Features of the Electron Density Distribution. In Theoretical Models of Chemical Bonding Part 2; Maksic, Z. B., Ed.: Springer: Berlin, 1990.
26. (c) Bader, R. F. W.; Popelier, P. L. A.; Keith, T. A. Angew. Chem., Int. Ed. Engl. 1994, 33, 620.
27. (a) Holmes, R. R.; Deiters, J. A. J. Am. Chem. Soc. 1977, 99, 3318.
28. (b) Holmes, R. R.; Day, R. O.; Harland, J. J.; Sau, A. C.; Holmes, J. M. Organometallics 1984, 3, 341.
29. 24, which is defined as the angle between normals of the two planes 1-2-4 and 5-2-4, was selected so as to be the smallest angle among nine dihedral angles. (figure presented)
30. The MP2 results give slightly longer bond lengths than the HF calculations. See: Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986; pp 194-197.
31. (a) Holmes, R. R. Chem. Rev. 1990, 90, 17.
32. (b) Ugi, I.; Marquarding, D.; Klusacek, H.; Gillespie, P. Acc. Chem. Rev. 1971, 4, 288.
33. 9 See also: Ayala, P. Y.; Schlegel, H. B. J. Chem. Phys. 1997, 107, 375.
34. Corriu, R. J. P.; Guerin, C.; Moreau, J. J. E. The Chemistry of Organic Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, U.K., 1989; pp 305-370.
35. Omoto, K.; Sawada, Y.; Fujimoto, H. J. Am. Chem. Soc. 1996, 118, 1750.
36. (a) Carpenter, J. E.; Weinhold, F. J. Mol. Struct. (THEOCHEM) 1988, 169, 41.
37. (b) Foster, J. P.; Weinhold, F. J. Am. Chem. Soc. 1980, 102, 7211.
38. (c) Reed, A. E.; Weinhold, F. J. Chem. Phys. 1985, 83, 1736.
39. (d) Reed, A. E.; Weinhold, F. J. Chem. Phys. 1983, 78, 4066
40. (e) Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys, 1985, 83, 735.
41. (f) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
42. inv is assigned to be a strongly distorted TBP structure, it may be regarded as a tetracoordinate structure around the silicon center.
43. A (3,-1) critical point means that two curvatures of the Laplacian of ρ are negative (zρ is a maximum at this point) along two axes in the corresponding plane and a curvature is positive (ρ is a minimum at this point) along the third axis which is perpendicular to the plane. A (3,+1) critical point means that two curvatures of the Laplacian of ρ are positive (ρ is a minimum at this point) along two axes in the corresponding plane and a curvature is negative (ρ is a maximum at this point) along the third axis which is perpendicular to the plane.
44. 4 are reported to be 85.6, 74.4, 59.5, 51.9 kcal/mol for M = C, Si, Ge, and Sn, respectively: Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 1, p 5.