Mechanism of Amine and Amide Ion Substitution Reactions at the Carbon-Nitrogen Double Bond

Journal of Organic Chemistry

Volumn 50, Issue 18, 1985, Pages 3348-3355

  Johnson, James Elver ^a   Ghafouripour, Abdolkarim ^a   Arfan, Mohammad ^a   Todd, Susan L ^a   Sitz, Deborah A ^a  

^a TEXAS WOMAN'S UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0009175949     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00218a021     Document Type: Article

References (23)

1. Ta-Shma, R.; Rappoport, Z. Tetrahedron Lett. 1971, 3813–3816.
2. Ta-Shma, R.; Rappoport, Z. J. Am. Chem. Soc. 1976, 98, 8460–8467.
3. Ta-Shma, R.; Rappoport, Z. J. Am. Chem. Soc. 1977, 99, 1845–1858.
4. Ta-Shma, R.; Rappoport, Z. J. Chem. Soc., Perkin Trans. 2 1977, 659–667. (5) Johnson, J. E.; Nalley, E. A.; Weidig, C. J. Am. Chem. Soc. 1973, 95, 2051–2052.
5. Johnson, J. E.; Nalley, E. A.; Weidig, C.; Arfan, M. J. Org. Chem. 1981, 46, 3623-3629. (7) McCormack, M. T.; Hegarty, A. F. Tetrahedron Lett. 1976, 395-396.
6. Hegarty, A. F.; McCormack, M. T.; Hathaway, B. J.; Hulett, L. J. Chem. Soc., Perkin Trans. 2 1977, 1136-1141.
7. Rowe, J. E.; Hegarty, A. F. J. Org. Chem. 1984, 49, 3083–3087.
8. (a) Deslongchamps, P. “Stereoelectronic Effects in Organic Chemistry” Pergamon: Elmford, NY, 1983. (b) For an alternate view-point see: Hosie, L.; Marshall, P. J.; Sinnott, M. L. J. Chem. Soc., Perkin Trans. 2 1984, 1121–1131.
9. Similar isomerizations have been reported: Dignam, K. J.; Hegarty, A. F. J. Chem. Soc., Perkin Trans. 2 1979, 1437–1443.
10. Johnson, J. E.; Springfield, J. R.; Hwang, J. S.; Hayes, L. J.; Cunningham, W. C.; McClaugherty, D. L. J. Org. Chem. 1971, 36, 284–294.
11. Johnson, J. E.; Nalley, E. A.; Kunz, Y. K.; Springfield, J. R. J. Org. Chem. 1976, 41, 252–259. The stereochemical assignments for the (Z)-and (E)-hydroximoyl chlorides should be reversed in this paper.
12. The configurations of 7g-i are assumed to be Z in analogy with p-nitrobenzamidoxime which exists in the Z configuration: Arte, E.; Declerq, J. P.; Germain, G.; Van Meersche, M. Bull. Soc. Chem. Belg. 1978, 87, 573–578.
13. Weissberger, A., Ed. “Techniques of Organic Chemistry, Vol. 7: Organic Solvents”, 2nd ed.; Interscience: New York, 1955.
14. (a) Page, M. I.; Jencks, W. P. J. Am. Chem. Soc. 1972, 94, 8828–8838. (b) Page, M. I.; Jencks, W. P. J. Am. Chem. Soc. 1972, 94, 8818–8827. (23) Bender, M. L.; Jones, J. M. J. Am. Chem. Soc. 1962, 27, 3771–3774.
15. Sneen, R. A. Acc. Chem. Res. 1973, 6, 46–53.
16. Johnson, J. E.; Cornell, S. C. J. Org. Chem. 1980, 45, 4144–4148.
17. (a) McCormack, M. T.; Hegarty, A. F. J. Chem. Soc., Perkin Trans. 2, 1976, 1701-1709. (b) Hegarty, A. F. Acc. Chem. Res. 1980, 13, 448–454.
18. (a) Johnson, J. E.; Ghafouripour, A.; Haug, Y. K.; Cordes, A. W.; Pennington, W. T.; Exner, O. J. Org. Chem. 1985, 50, 993–997. (b) Bertolasi, V.; Sacerdoti, M.; Tossi, D. Cryst. Struct. Commun. 1977, 6, 335–341. (29) Miller, S. I. Tetrahedron 1977, 33, 1211–1217.
19. Stirling, C. J. Acc. Chem. Res. 1979, 12, 198–203.
20. Barnett, R. E.; Jencks, W. P. J. Am. Chem. Soc. 1969, 91, 2358–2369.
21. Bernasconi, C. F. Acc. Chem. Res. 1978, 11, 147–152. (33) (a) Orvik, J. A.; Bunnett, J. F. J. Am. Chem. Soc. 1970, 92, 2417–2427. (b) Kirby, A. J.; Jencks, W. P. J. Am. Chem. Soc. 1965, 87, 3217–3224.
22. Brewis, D. M.; Chapman, N. B.; Paine, J. S.; Shorter, J.; Wright, D. J. J. Chem. Soc., Perkin Trans. 2 1974, 1787-1801.
23. Kevill, D. N.; Daum, P. H.; Sapre, R. J. Chem. Soc., Perkin Trans. 2 1975, 963–965.