Mechanism of elimination from (1-anilino-1-cyanoethyl)benzene promoted by sodium methoxide in methanol

Journal of Organic Chemistry

Volumn 61, Issue 16, 1996, Pages 5656-5658

  Cho, Bong Rae ^a   Oh, Yoon Chul ^a   Lee, Sang Hae ^a   Park, Young Ja ^b  

^a Korea University   (South Korea)

^b Sookmyung Women's University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0013474920     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960254w     Document Type: Article

References (18)

1. Hoffman, R. V.; Bartsch, R. A.; Cho, B. R. Acc. Chem. Res. 1989, 22, 211-217.
2. Cho, B. R.; Pyun, S. Y. J. Am. Chem. Soc. 1991, 113, 3920-3924.
3. 5 indicating that the N-H and C-X bonds are stronger than the C-H and N-X bonds.
4. Dean, J. A. Handbook of Organic Chemistry; McGraw-Hill: New York, 1987; pp 3-13-3-37.
5. 7 Although the corresponding values determined in MeOH are not available in the literature, the relative acidities may be assumed to be nearly the same in both solvents.
6. Bordwell, F. G. Acc. Chem. Res. 1986, 21, 456-463.
7. Dew, E. N.; Richie, P. D. Chem. Ind. 1969, 51-52.
8. Bartsch, R. A.; Zavada, J. Chem. Rev. 1980, 80, 453-494.
9. Bartsch, R. A.; Cho, B. R. J. Am. Chem. Soc. 1979, 101, 3587-3591.
10. 12 reveals that the gas phase structure is very similar to that in the solid state except that the dihedral angle between the N-H and C-CN bonds is 81.605°. Therefore, it seems reasonable to assume that the solution-state structure for 3a should also be similar to that in the solid-state.
11. Gaussian 94, Gaussian Inc., Pittsburgh, PA, 1995.
12. (a) Gold, V; Morris, K. P.; Wilcox, C. F. J. Chem. Soc., Perkin Trans. 2 1982, 1615-1620.
13. (b) More O'Ferall, R. A. J. Chem. Soc., Chem. Commun. 1969, 114-115.
14. (a) Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry; Harper and Row: New York, 1987; pp 591-560.
15. (b) Gandler, J. R. In The Chemistry of Double Bonded Functional Groups; Patai, S., Ed.; Wiley: Chichester, 1989; Vol. 2, Part 1, pp 734-797.
16. Cary, F. A.; Sundberg, R. J. Advanced Organic Chemistry, 3rd ed.; Plenum Press: New York, 1990; Part A, pp 196-209.
17. Sheldrick, G. M. SHELXS-86 and SHELXL-93, Program for Crystal Structure Determination; Cambridge University Press: Cambridge, 1986, 1993.
18. The author has deposited atomic coordinates for (1-anilino-1-cyanoethyl)benzene with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.