17 O NMR spectra of α,β-unsaturated carbonyl compounds RCH=CHCOX: The influence of group X on the δ(17 O) value of the carbonyl oxygen and on the shielding effect of group R

Molecules

Volumn 4, Issue 11, 1999, Pages 320-328

  Zhuo, Jin Cong ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

17O NMR; Carbonyl groups; Resonance effects; , unsaturated carbonyl compounds

Indexed keywords

CARBONYL DERIVATIVE; METHYL GROUP; OXYGEN; PHENYL GROUP; SOLVENT;

ARTICLE; CHEMICAL BOND; ELECTRON TRANSPORT; NUCLEAR MAGNETIC RESONANCE; QUALITATIVE ANALYSIS; TEMPERATURE DEPENDENCE;

EID: 4344574831     PISSN: 14203049     EISSN: None     Source Type: Journal    
DOI: 10.3390/41100320     Document Type: Article

References (37)

1. Boykin, W. D. (Ed.). O-17 NMR Spectroscopy in Organic Chemistry; CRC Press, Boca raton: FL, 1991.
2. a) Dahn, H.; Péchy, P.; Toan, V. V. Angew. Chem. Int. Ed. Engl. 1990, 29, 647;
3. b) Dahn, H.; Carrupt, P.-A. Magn. Reson. Chem. 1997, 35, 577;
4. c) Dahn, H.; Péchy, P.; Toan, V. V. Magn. Reson. Chem. 1997, 35, 589;
5. d) Christ, H. A.; Diehl, P.; Schneider, H. P.; Dahn, H. Helv. Chim. Acta 1961, 44, 865.
6. a) Patai, S.; Rappoport, Z. (Eds.). The chemistry of Enones; Wiley: Chichester, 1989;
7. b) Habermas, K. L.; Denmark, S. E.; Jones, T. K. Org. React. 1994, 45, 1;
8. c) Reich, H. J.; Wollowitz, S. Org. React. 1993, 44, 1;
9. d) Crimmins, M. T.; Reinhold, T. L. Org. React. 1993, 44, 297;
10. e) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135;
11. f) Chapdelaine, M. J.; Hulce, M. Org. React. 1990, 38, 225;
12. g) Nagata, W.; Yoshioka, M. Org. React. 1977, 25, 225;
13. h) Caine, D. Org. React. 1976, 23, 1;
14. i) House, H. O. Acc. Chem. Res. 1976, 9, 59.
15. March, J. Advanced Organic Chemistry, 4th Ed.; Wiley: Chichester, 1992.
16. a) Kalinowski, H.-O.; Berger, S.; Braun, S. Carbon-13 NMR Spectroscopy; Wiley: Chichester, 1988;
17. b) Hansen, P. E. in Supplement A: The Chemistry of Double-bonded Functional Groups; Patai, S., Ed.; Wiley: Chichester, 1989; Vol. 2, p 81.
18. Zhuo, J.-C. Magn. Reson. Chem. 1997, 35, 719.
19. Dahn, H.; Péchy, P.; Toan, V. V. Magn. Reson. Chem. 1990, 28, 883.
20. Delseth, C.; Nguyen, T. T.-T.; Kintzinger, J.-P. Helv. Chim. Acta 1980, 63, 498.
21. Zhuo, J.-C. Magn. Reson. Chem. 1996, 34, 595.
22. Rabinovich, D. J. Chem. Soc. (B) 1970, 11.
23. Balakrishnan, P.; Baumstark, A. L.; Boykin, D. W. Org. Magn. Reson. 1984, 22, 753.
24. Exner, O. Correlation Analysis of Chemical Data; Plenum Press: New York, 1988.
25. Hammen, P. D.; Braisted, A. C.; Northrup, D. L. Synth. Commun. 1991, 21, 2157.
26. John, R. A.; Schmid, V.; Wyler, H. Helv. Chim. Acta 1987, 70, 600.
27. Jacobi, P. A.; Cai, G. Heterocycles 1993, 35, 1103.
28. a) Sinisterra, J. V.; Garcia-Raso, A.; Cabello J. A.; Marinas, J. M. Synthesis 1984, 502;
29. b) Conia, M. J.-M. Bull Soc. Chim. Fr. 1956, 1392.
30. a) Le Corre, M. C. R. Acad. Sci. Paris Serie C 1970, 270, 1312;
31. b) Meijer, L. H. P.; Pandit, U. K. Tetrahedron 1985, 41, 467.
32. Mead, D.; Loh, R.; Asato A. E.; Liu, R. S. H. Tetrahedron Lett. 1985, 26, 2873.
33. Schummer, A.; Yu, H.; Simon, H. Tetrahedron 1991, 47, 9019.
34. Ananda, G. D. S.; Cremins, P. J.; Stoodley, R. J. J. Chem. Soc. Chem. Commun. 1987, 882.
35. Schnabel, H. W.; Grimm, D.; Jensen, H. Justus Liebigs Ann. Chem. 1974, 477.
36. Tamura, Y.; Yoshimoto, Y.; Kunimoto, K.; Tada, S.; Tomita, T.; Wada, T.; Seto, E.; Murayama, M.; Shibata, Y.; Nomura, A.; Ohata, K. J. Med. Chem. 1977, 20, 709.
37. Zhuo, J.-C. unpublished results.