Theoretical Transition Structures for Hydride Transfer to Methyleniminium Ion from Methylamine and Dihydropyridine: On the Nonlinearity of Hydride Transfers

Journal of the American Chemical Society

Volumn 109, Issue 7, 1987, Pages 2226-2227

  Wu, Yun Dong ^a   Houk, K N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845282135     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00241a074     Document Type: Article

References (14)

1. Wu, Y. D.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 906.
2. Applications of Biochemical Systems in Organic Chemistry; Jones, J. B., Sih, C. J., Perlman, D. Eds.; Wiley: New York, 1976.
3. Meyers, A. I.; Openlaender, T. J. Am. Chem. Soc. 1986, 108, 1989 and references therein.
4. Binkley, J. S.; Frisch, M.; Krishnan, R.; DeFrees, D.; Schlegel, H. B.; Whiteside, R. A.; Fluder, E.; Seeger, R.; Peope, J. A. GAUSSIAN 82, Carnegie-Mellon University, Pittsburgh, PA.
5. Huttley, B. G.; Mountain, A. E.; Williams, 1. H.; Maggiora, G. M.; Schowen, R. J. J. Chem. Soc., Chem. Commun. 1986. 267. Professor Schowen has informed us that the C2h structure does indeed have a second imaginary frequency of 25 cm'1 and that the 3-21G surface is very flat in the region of this stationary point.
6. Van der Kerk, S. M.; Van Gerresheim, W., Verhoeven, J. W. Red. Trav. Chim. Pavs-Bas 1984, 103, 143.
7. Verhoeven, J. W.; Van Gerresheim, W. O.; Martens, F. M.; van der Kerk, S. M. Tetrahedron 1986, 42, 975.
8. Powell, M. F.; Bruice, T. C. J. Am. Chem. Soc. 1983. 105, 1041.
9. Ohno, A.; Ikegushi, M.; Kimura, T.; Oka, S. J. am. Chem. Soc. 1979, 101, 7036.
10. Sheldon, J. S.; Bowie, J.; Hayes, M. S. Nouv. J. Chim. 1984, 8. 79.
11. de Kok, P. M. T.; Donkersloot, M. C. A.; van Lieu, P. M.; Meulen-dijks, G. H. W. M.; Bastiaansen, L. A. M.; Van Hooff, H. J. G.; Kanters, J. A.; Buck, H. M. Tetrahedron 1986, 42. 941.
12. Dihydropyridine is planar: Raber, D. J.; Rodriguez. W. J. Am. Chem. Soc. 1985. 107, 4146.
13. Benner, S. A.; Nambiar, K. P.; Chambers, G. K. J. K. J. Am. Chem. Soc. 1985, 107, 5513. Nambiar. K.: Stauffer, D. M.; Kolodziej, P. A.; Benner, S. A. J. Am. Chem. Soc. 1983. 105, 5886. Benner, S. A. Experientia 1982, 38, 633.
14. Houk. K. N.; Paddon-Row, M. N.; Rondan, N. G.; Wu, Y. D.; Brown, F. K.; Spellmeyer, D. C.; Metz, J. T.; Li, Y. Loncharich, R. J. Science (Washington, D. C.) 1986, 231, 1108 and references therein.