Synthesis and NMR spectral analysis of amine heterocycles: The effect of asymmetry on the 1H and 13C NMR spectra of N,O-acetals

Journal of Chemical Education

Volumn 84, Issue 6, 2007, Pages 1011-1013

  Saba, Shahrokh ^a   Ciaccio, James A ^a   Espinal, Jennifer ^a   Aman, Courtney E ^a  

^a FORDHAM UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LIGANDS; NUCLEAR MAGNETIC RESONANCE; PURIFICATION; SPECTRUM ANALYSIS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ACETALS; HETEROCYCLES; METHYL; SPECTRAL EFFECTS;

AMINES;

EID: 34249821631     PISSN: 00219584     EISSN: None     Source Type: Journal    
DOI: 10.1021/ed084p1011     Document Type: Article

References (22)

1. Hesse, M. Alkaloids: Nature's Curse or Blessing; Wley-VCH: Weinheim, Germany, 2002.
2. Franzen, F.; Eysell, K. Biologically Active Amines Found in Man: Their Biochemistry, Pharmacology, and Pathophysiological Importance; Pergamon: New York, 1969.
3. Kumar, A. M. in Separation Techniques in Clinical Chemistry; Aboul-Enein, H. Y., Ed.; Marcel Dekker: New York, 2003; pp 289-320.
4. Mukade, T.; Dragoli, D. R.; Ellman, J. A. J. Comb. Chem. 2003, 5, 590-596.
5. Bryson, T. A.; Bonitz, G. H.; Reichel, C. J.; Dardis, R. E. J. Org. Chem. 1980, 45, 524-525.
6. Eliel, E. L. J. Chem. Educ. 1980, 57 52-56.
7. For another example of an experiment illustrating the diastereotopicity of ligands within a chiral molecule, see Brisbois, R. G.; Batterman, W. G.; Kragerud, S. R. J. Chem. Educ. 1997, 74, 834-835.
8. Brown, W. H.; Foote, C. S.; Iverson, B. L. Organic Chemistry, 4th ed.; Thomson Brooks/Cole: Belmont, CA, 2005; pp 917-918.
9. Baxter, E. W.; Reitz, A. B. Organic Reactions 2002, 59, 1-714.
10. Carlson, M. W.; Ciszewski, J. T.; Bhatti, M. M.; Swanson, W. F.; Wilson, A. M. J. Chem. Educ. 2000, 77, 270-271.
11. Saavedra, J. E. J. Org. Chem. 1985, 50, 2271-2273.
12. Alva Astudillo, M. E.; Chokotho, N. C. J.; Jarvis, T. C.; Johnson, C. D.; Lewis, C. C.; McDonnell, P. D. Tetrahedron 1985, 41, 5919-5928.
13. Collard, D. M.; Jones, A. G.; Kriegel, R. M. J. Chem. Educ. 2001, 78, 70-72.
14. Rablen, P. R.; Deuber, M. A.; Lim, A. C.; Dickson, R. M.; Wintner, C. E. J. Chem. Educ. 1991, 68, 796-797.
15. Rowland, A. T. J. Chem. Educ. 1983, 60, 1084-1085.
16. Paulson, D. R.; Hartwig, A. L.; Moran, G. F. J. Chem. Educ. 1973, 50, 216-217.
17. Marchand, A. P. J. Chem. Educ. 1972, 49, 841-843.
18. Bergmann, E. D. Chem. Rev. 1953, 53, 309-352.
19. Agami, C.; Couty, F. Eur. J. Org. Chem. 2004, 677-685.
20. Shen, M.; Li, C. J. Org. Chem. 2004, 69, 7906-7909.
21. Adam, W.; Schambony, S. B. Org. Lett. 2001, 3, 79-82.
22. Cann, M. C.; Connelly, M. E. Real-World Cases in Green Chemistry; American Chemical Society: Washington, DC, 2000.