Evaluation of β- and γ-effects of group 14 elements using intramolecular competition

Journal of Organic Chemistry

Volumn 65, Issue 10, 2000, Pages 3135-3142

  Sugawara, Masanobu ^a   Yoshida, Jun Ichi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; GEOMETRY; MOLECULAR INTERACTION;

EID: 0034686070     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991977t     Document Type: Article

References (72)

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64. Reactivities of allylsilanes, allylgermanes, and allylstannanes with carbenium ions has been studied extensively. See ref 6n.
65. For example, Bassindale, A. R.; Taylor, P. G. The chemistry of organic silicon compounds; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1989; pp 839-892.
66. Yoshida, J.; Tsujishima, H.; Nakano, K.; Isoe, S. Inorg. Chim. Acta 1994, 220, 129-135.
67. It has been reported that a disilanyl group is able to enhance the β effect of silicon in the electrophilic reaction of vinylsilane. Dixon, T. A.; Steele, K. P.; Weber, W. P. J. Organomet. Chem. 1982, 231, 299.
68. + (M = Si, Ge, Sn) were reported in the literature. Nguyen, K. A.; Gordon, M. S.; Wang, G.-T.; Lambert, J. B. Organometallics 1991, 10, 2798-2803.
69. For example, (a) Sieber, S.; Buzek, P.; Schleyer, P. v. R.; Koch, W.; Carneiro, J. W. de M. J. Am. Chem. Soc. 1993, 115, 259-270. (b) Saunders, M.; Vogel, P.; Hagen, E. L.; Rosenfeld, J. Acc. Chem. Res. 1973, 6, 53-59. (c) Collins, C. J. Chem. Rev. 1969, 69, 534-550.
70. For example, (a) Sieber, S.; Buzek, P.; Schleyer, P. v. R.; Koch, W.; Carneiro, J. W. de M. J. Am. Chem. Soc. 1993, 115, 259-270. (b) Saunders, M.; Vogel, P.; Hagen, E. L.; Rosenfeld, J. Acc. Chem. Res. 1973, 6, 53-59. (c) Collins, C. J. Chem. Rev. 1969, 69, 534-550.
71. For example, (a) Sieber, S.; Buzek, P.; Schleyer, P. v. R.; Koch, W.; Carneiro, J. W. de M. J. Am. Chem. Soc. 1993, 115, 259-270. (b) Saunders, M.; Vogel, P.; Hagen, E. L.; Rosenfeld, J. Acc. Chem. Res. 1973, 6, 53-59. (c) Collins, C. J. Chem. Rev. 1969, 69, 534-550.
72. Gaussian 98, Revision A.7, 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.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 1998.