Elimination Reactions of (E)- and (Z)-Benzaldehyde O-Pivaloyloximes. Transition-State Differences for the Syn and Anti Eliminations Forming Nitriles

Journal of Organic Chemistry

Volumn 62, Issue 7, 1997, Pages 2230-2233

  Cho, Bong Rae ^a   Cho, Nam Soon ^a   Lee, Sang Kook ^a  

^a Korea University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001383516     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9618637     Document Type: Article

References (23)

1. Saunders, W. H., Jr.; Cockerill, A. F. Mechanism of Elimination Reactions; Wiley: New York, 1973; (a) Chapter 1-4, (b) pp 498-531.
2. Bartsch, R. A.; Zavada, J. Chem. Rev. 1980, 80, 453-494.
3. Gandler, J. R. In The Chemistry of Double Bonded Functional Groups; Patai, S., Ed.; Wiley: Chichester, 1989; Vol. 2, Part 1, pp 734- 797.
4. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry; Harper and Row: New York, 1987; pp 591-616.
5. Hegarty, A. F.; Tuohey, P. J. J. Chem. Soc., Perkin Trans 2 1980, 1313-1317.
6. Cho, B. R.; Kim, K. D.; Lee, J. C.; Cho, N. S. J. Am. Chem. Soc. 1988, 110, 6145-6148.
7. Cho, B. R.; Lee, J. C.; Cho, N. S.; Kim, K. D. J. Chem. Soc., Perkin Trans 2, 1989, 489-492.
8. Cho, B. R.; Min, B. K.; Lee, C. W.; Je, J. T. J. Org. Chem. 1991, 56, 5513-5516.
9. Cho, B. R.; Kim, K. D.; Lee, J. C.; Cho, N. S. J. Am. Chem. Soc. 1991, 110, 6145.
10. Cho, B. R.; Jung, J.; Ahn, E. K. J. Am. Chem. Soc. 1992, 114, 3425-3458.
11. Cho, B. R.; Je, J. T. J. Org. Chem. 1993, 58, 6190-6193.
12. Cho, B. R.; Maing Yoon, C.-O.; Song, K. S. Tetrahedron Lett. 1995, 36, 3193-3196.
13. Cho, B. R.; Jang, W. J.; Bartsch, R. A. J. Org. Chem. 1993, 58, 3901-3904.
14. 3 Therefore, it seems reasonable to ascribe the same E2 mechanism to the eliminations from 1.
15. Cho, B. R.; Chung, H. S.; Cho, N. S. unpublished results.
16. Oediger, H.; Moller, F.; Eiter, K. Synthesis 1972, 591-598
17. Wolkoff, P. J. Org. Chem. 1982, 47, 1944-1948.
18. Smith, P. J. In Isotopes in Organic Chemistry; Buncel, E., Lee, C. C., Eds.; Elsevier: Amsterdam, 1976; pp 239-241.
19. Bach, R. D.; Badger, R. C.; Lang, T. J. J. Am. Chem. Soc. 1979, 101, 2845-2848. Gandler, J. R.; Jencks, W. P. J. Am. Chem. Soc. 1982, 104, 1937-1951.
20. Bach, R. D.; Badger, R. C.; Lang, T. J. J. Am. Chem. Soc. 1979, 101, 2845-2848. Gandler, J. R.; Jencks, W. P. J. Am. Chem. Soc. 1982, 104, 1937-1951.
21. Schoenewaldt, F. E.; Kinnel, R. B.; Paul Davis, P. J. Org. Chem. 1968, 33, 4270-4272
22. Coetzee, J. F. Prog. Phys. Org. Chem. 1965, 4, 45-92.
23. Gaussian 94, Revision A.1: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Peterson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Lahman, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foreman, J. B.; Ciolowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogie, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, M.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian, Inc.: Pittsburgh, PA, 1995.