SN2 substitution on sp2 nitrogen of protonated oxime

Chemistry Letters

Volumn , Issue 2, 1998, Pages 111-112

  Mori, Seiji ^a   Uchiyama, Katsuya ^a   Hayashi, Yujiro ^a   Narasaka, Koichi ^a   Nakamura, Eiichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0032373249     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.111     Document Type: Article

References (25)

1. a) H. Kusama, Y. Yamashita, and K. Narasaka, Chem. Lett., 1995, 5.
2. b) H. Kusama, K. Uchiyama, Y. Yamashita, and K. Narasaka, Chem. Lett., 1995, 715.
3. c) H. Kusama, Y. Yamashita, K. Uchiyama, and K. Narasaka, Bull. Chem. Soc. Jpn., 70, 965 (1997).
4. T. Okuyama and M. Ochiai, J. Am. Chem. Soc., 119, 4785 (1997).
5. a) R. E. Gawley, Org. React., 35, 1 (1988).
6. b) K. Maruoka and H. Yamamoto, "Functional Group Transformations via Carbonyl Derivatives, in Comprehensive Organic Synthesis", ed. by B. M. Trost and I. Fleming, Vol. 6, p. 763, Pergamon Press, Oxford, UK (1991).
7. c) A. Guy and J. P. Guetté, Synthesis, 1980, 222.
8. a) GAUSSIAN 94. Revision B.2, M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, and J. A. Pople, GAUSSIAN Inc.; Pittsburgh, PA, 1995.
9. b) W. J. Hehre, L. Radom, P. v. R. Schleyer, and J. A. Pople, "Ab Initio Molecular Orbital Theory"; John Wiley; New York, USA (1986).
10. MP2(FC) (FC = frozen core): C. Møller and M. S Plesset. Phys. Rev., 46, 618-622 (1934); J. A. Pople, R. Krishman, H. B. Schlegel, and J. S. Binkley, Int. J. Quantum. Chem. Symp., 13, 225 (1979).
11. MP2(FC) (FC = frozen core): C. Møller and M. S Plesset. Phys. Rev., 46, 618-622 (1934); J. A. Pople, R. Krishman, H. B. Schlegel, and J. S. Binkley, Int. J. Quantum. Chem. Symp., 13, 225 (1979).
12. M. T. Nguyen, G. Raspoet, and L. G. Vanquickenborne, J. Am. Chem. Soc., 119, 2552 (1997).
13. s) is -1.36 eV and that of the π*-orbital (LUMO+1) is -1.22 eV (HF/6-31G*//HF/6-31G*).
14. Orbital transformation was carried out with the B3LYP/6-31G* wave function for the MP2-optimized geometry. See: a) S. F. Boys, "Quantum Theory of Atoms, Molecules, and the Solid State"; ed by P. O. Lowdin Academic Press: New York, USA (1968), p.253.
15. b) A. D. Becke, J. Chem. Phys., 98, 5648 (1993); C. Lee, W. Yang, and R. G. Parr, Phys. Rev. B , 37, 785 (1988).
16. b) A. D. Becke, J. Chem. Phys., 98, 5648 (1993); C. Lee, W. Yang, and R. G. Parr, Phys. Rev. B , 37, 785 (1988).
17. c) E. Nakamura, S. Mori, M. Nakamura, and K. Morokuma, J. Am. Chem. Soc., 119, 4887 (1997).
18. Surface generated by MOLDEN 3.2, implemented by G. Schaftenaar, CAOS/CAMM Center, Netherland (1997).
19. a) V. Lucchini, G. Modena, and L. Pasquato, J. Am. Chem. Soc., 117, 2297 (1995).
20. b) M. N. Glukhovtsev, A. Pross, and L. Radom, J. Am. Chem. Soc., 116, 5961 (1994).
21. a) R. Griot and T. Wagner-Jauregg, Helv. Chim. Acta, 41, 867 (1958); 42, 121 (1959).
22. a) R. Griot and T. Wagner-Jauregg, Helv. Chim. Acta, 41, 867 (1958); 42, 121 (1959).
23. b) D. Schinzer and Y. Bo, Angew. Chem., Int. Ed. Engl., 30, 687 (1991).
24. c) E. Erdik and M. Ay, Chem. Rev., 89, 1947 (1989).
25. d) M. Hamana, H. Noda, and J.-I. Uchida, Yakugaku Zasshi, 90, 1001 (1970).