A simple and convenient method for generation and NMR observation of stable carbanions: An advanced undergraduate laboratory experiment

Journal of Chemical Education

Volumn 76, Issue 6, 1999, Pages 830-834

  Kasmai, Hamid S ^a  

^a EAST TENNESSEE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0004365050     PISSN: 00219584     EISSN: None     Source Type: Journal    
DOI: 10.1021/ed076p830     Document Type: Article

References (24)

1. For example, see: Hehre, W. J.; Burke, L. D.; Shusterman, A. J.; Pietro, W. J. Experiments in Computational Organic Chemistry; Wavefunction: Irvine, CA, 1993.
2. Lansbury, P. T. J. Chem. Educ. 1961, 38, 307.
3. (a) Schaefer, T.; Schneider, W. G. Can. J. Chem. 1963, 41, 966.
4. (b) Grutzner, J. B.; Lawlor, J. M.; Jackman, L. M. J. Am. Chem. Soc. 1972, 94, 2306. (c) Taylor, G. A.; Rakita, P. E. Org. Magn. Res. 1974, 6, 644.
5. (c) Taylor, G. A.; Rakita, P. E. Org. Magn. Res. 1974, 6, 644.
6. Williamson, K. L. Macroscale and Microscale Organic Exeriments; D. C. Heath: Lexington, MA, 1994.
7. Anastassiou, A. G.; Kasmai, H. S.; Saadein, M. R. Tetrahedron Lett. 1980, 21, 3743.
8. Noller, C. R. J. Chem. Educ. 1949, 26, 429.
9. Price, G. G.; Whiting, M. C. Chem. Ind. 1963, 775. Ritchie, C. D.; Uschold, R. E. J. Am. Chem. Soc. 1967, 89, 2960. Matthews, W.; Bares, J. E.; Bartmess, J. E.; Bordwell, F. G.; Cornforth, F. J.; Drucker, G. E.; Margolin, Z.; McCallum, R. J.; McCollum, G. J.; Vanier, N. R. J. Am. Chem. Soc. 1975, 92, 7006.
10. Price, G. G.; Whiting, M. C. Chem. Ind. 1963, 775. Ritchie, C. D.; Uschold, R. E. J. Am. Chem. Soc. 1967, 89, 2960. Matthews, W.; Bares, J. E.; Bartmess, J. E.; Bordwell, F. G.; Cornforth, F. J.; Drucker, G. E.; Margolin, Z.; McCallum, R. J.; McCollum, G. J.; Vanier, N. R. J. Am. Chem. Soc. 1975, 92, 7006.
11. Price, G. G.; Whiting, M. C. Chem. Ind. 1963, 775. Ritchie, C. D.; Uschold, R. E. J. Am. Chem. Soc. 1967, 89, 2960. Matthews, W.; Bares, J. E.; Bartmess, J. E.; Bordwell, F. G.; Cornforth, F. J.; Drucker, G. E.; Margolin, Z.; McCallum, R. J.; McCollum, G. J.; Vanier, N. R. J. Am. Chem. Soc. 1975, 92, 7006.
12. Streitwieser, A. Jr.; Ciuffarin, E.; Hammons, J. H. J. Am. Chem. Soc. 1967, 89, 63.
13. 6 was employed for the generation and observation of a phosphorus ylide intermediate: Breton, G. W. J. Chem. Educ. 1997, 74, 114.
14. Kaufman, M. J.; Gronert, S.; Streitwieser, A. Jr. J. Am. Chem. Soc. 1988, 110, 2829 and references therein.
15. Olmstead, W. N.; Bordwell, F. G. J. Org. Chem. 1980, 45, 3299.
16. Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456.
17. 6.
18. (b) Faure, R.; Assef, V. G.; Kister, J.; Metzger, J. Org. Magn. Res. 1977, 9, 688.
19. (a) Fraenkel, G.; Carter, R. E.; McLachlan, A.; Richards, J. H. J. Am. Chem. Soc. 1960, 82, 5846.
20. (b) Breitmaier, E.; Voelter, W. Carbon-13 NMR Spectroscopy; VCH: New York, 1989.
21. Anastassiou, A. G.; Kasmai, H. S. Angew. Chem. Int. Ed. Engl. 1980, 19, 43.
22. Kasmai, H. S.; Liu, R. J. Chem. Soc., Perkin Trans. 2 1997, 1605.
23. Saadein, M. R. Ph.D. Thesis, Syracuse University, Syracuse, NY, 1984.
24. For example see: Breitmaier, E.; Hollstein, U. Org. Magn. Res. 1976, 8, 573.