NMR of enaminones. Part 6† - 17O and 13C NMR study of tautomerization in Schiff bases

Magnetic Resonance in Chemistry

Volumn 37, Issue 4, 1999, Pages 259-268

  Zhuo, Jin Cong ^a,b  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

^b OHIO STATE UNIVERSITY   (United States)

Author keywords

13C NMR; 17O NMR; NMR; Schiff bases; Tautomeric equilibrium

Indexed keywords

NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

13C NMR; 17O NMR; CYCLOHEXANONES; ENAMINONES; NMR DATA; NMR SPECTRUM; NMR STUDIES; SCHIFF-BASE; TAUTOMERIC EQUILIBRIA; TAUTOMERIZATIONS;

AMINES;

EID: 0033106576     PISSN: 07491581     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1097-458X(199904)37:4<259::AID-MRC442>3.0.CO;2-6     Document Type: Article

References (76)

1. 1. J.-C. Zhuo, Molecules 2, 31 (1997).
2. 2. (a) F. Hibbert, Adv. Phys. Org. Chem. 22, 113 (1986);
3. (b) P. Schuster, G. Zundel and C. Sandorfy (Eds), The Hydrogen Bond. Recent Developments in Theory and Experiments. North-Holland, Amsterdam (1976);
4. (c) J. Emsley, Struct. Bonding (Berlin) 57, 147 (1984);
5. (d) J. Emsley, Chem. Soc. Rev. 9, 91 (1980);
6. (e) F. Hibbert and J. Emsley, Adv. Phys. Org. Chem. 26, 255 (1991).
7. 3. (a) J. Dabrowski and Kamienska-Trela, J. Am. Chem. Soc. 98, 2826 (1976);
8. (b) J. W. Ledbetter, J. Phys. Chem. 72, 4111 (1968);
9. (c) P. W. Alexander and R. J. Sleet, Aust. J. Chem. 23, 1183 (1970);
10. (d) S. R. Salman, S. K. Kanber and L. K. Arsalan, Spectrosc. Lett. 24, 1153 (1991).
11. 4. (a) S. H. Alarcón, A. C. Olivieri, G. R. Labadie, R. M. Cravero and M. González-Sierra, Tetrahedron 51, 4619 (1995);
12. (b) S. H. Alarcón, A. C. Olivieri, R. M. Cravero, G. R. Labadie, and M. González-Sierra, J. Phys. Org. Chem. 8, 713 (1995);
13. (c) F. S. Kamounah and S. R. Salman, Spectrosc. Lett. 29, 656 (1996).
14. 5. (a) S.-F. Tan, K.-P. Ang and H. Jayachandran, J. Chem. Soc., Perkin Trans. 2 1011 (1983);
15. (b) B. A. Korolev and N. V. Kameneva, Russ. J. Gen. Chem. (Engl. Transl.) 65, 612 (1995);
16. (c) N. V. Kameneva and B. A. Korolev, Russ. J. Gen. Chem. (Engl. Transl.) 65, 618 (1995).
17. 6. (a) F. Milia, E. Hadjoudis and J. Seliger, J. Mol. Struct. 177, 191 (1988);
18. (b) J. Seliger, V. Zagar, R. Blinc, E. Hadjoudis and F. Milia, Chem. Phys. 142, 237 (1990);
19. (c) A. S. Shalabi and N. T. Abdel-Ghani, Egypt. J. Chem. 33, 345 (1990);
20. (d) M. E. L. Saraiva, C. F. G. Geraldes and V. M. S. Gil, Tetrahedron 44, 163 (1988);
21. (e) W. Turbeville and P. K. Dutta, J. Phys. Chem. 94, 4060 (1990).
22. 7. (a) G. O. Dudek, J. Am. Chem. Soc. 85, 694 (1963);
23. (b) G. O. Dudek and E. P. Dudek, J. Am. Chem. Soc. 86, 4283 (1964);
24. (c) N. M. D. Brown and D. C. Nonhebel, Tetrahedron 24, 5655 (1968);
25. (d) J. A. Connor, D. J. Fine and R. Price, J. Chem. Soc, Dalton Trans. 559 (1981);
26. (e) A. C. Olivieri, J. Chem. Soc. Perkin Trans. 2 85 (1990);
27. (f) S. R. Salman, R. D. Farrant and J. C. Lindon, Spectrosc. Lett. 24, 1071 (1991);
28. (g) S. R. Salman, J. C. Lindon R. D. Farrant and T. A. Carpenter, Magn. Reson. Chem. 31, 991 (1993);
29. (h) S. H. Alarcón, A. C. Olivieri and M. González-Sierra, J. Chem. Soc. Perkin Trans. 2 1067 (1994).
30. 8. (a) Von G. Dannhardt and T. Debaerdemaeker, Chem.-Ztg. 111, 310 (1987);
31. (b) M. A. V. Ribeiro Da Silva, M. D. M. C. Ribeiro Da Silva, J. P. A. Paiva, I. M. C. S. Nogueira, A. M. Damas, J. V. Barkley, M. M. Harding, M. J. Akello and G. Pilcher, J. Chem. Soc. Perkin Trans. 2 1765 (1993).
32. 9. (a) N. Hoshino, T. Inabe, T. Mitani and Y. Maruyama, Bull. Chem. Soc. Jpn. 61, 4207 (1988);
33. (b) T. Inabe, N. Hoshino, T. Mitani and Y. Maruyama, Bull. Chem. Soc. Jpn. 62, 2245 (1989);
34. (c) T. Inabe, I. Gautier-Luneau, N. Hoshino, K. Okaniwa, H. Okamoto, T. Mitani, U. Nagashima and Y. Maruyama, Bull. Chem. Soc. Jpn. 64, 801 (1991).
35. 10. (a) T. Inabe, I. Luneau, T. Mitani, Y. Maruyama and S. Takeda, Bull. Chem. Soc. Jpn. 67, 612 (1994);
36. (b) T. Inabe, N. Hoshino-Miyajima, I. Luneau, T. Mitani and Y. Maruyama, Bull. Chem. Soc. Jpn. 67, 622 (1994).
37. 11. (a) J. V. Greenhill, Chem. Soc. Rev. 6, 277 (1977);
38. (b) Z. Rappoport (Ed.), The Chemistry of Enamines, Part 1. Wiley, Chichester (1994).
39. 12. (a) J.-C Zhuo, Magn. Reson. Chem. 35, 21 (1997);
40. (b) J.-C. Zhuo, Magn. Reson. Chem. 35, 311 (1997);
41. (c) J.-C Zhuo, Magn. Reson. Chem. 35, 432 (1997).
42. 13. W. D. Boykin (Ed.), 0-77 NMR Spectroscopy in Organic Chemistry. CRC Press, Boca Raton, FL (1991).
43. 14. V. V. Lapachev, I. Ya. Mainagashev, S. A. Stekhova, M. A. Fedotov, V. P. Krivopalov and V. P. Mamaev, J. Chem. Soc., Chem. Commun. 494 (1985).
44. 15. (a) L. Kozerski and J. Dabrowski, Org. Magn. Reson. 5, 459 (1973);
45. (b) M. Tencer and J. Dabrowski, Spectrosc. Lett. 16, 351 (1983).
46. 16. J. W. Smith, in The Chemistry of the Amino Group, edited by S. Patai, Chapt. 4. Wiley, Chichester (1968).
47. 17. (a) J.-C. Zhuo, H. Wyler, P. Péchy and H. Dahn, Helv. Chim. Acta 77, 317 (1994);
48. (b) D. W. Boykin, S. Chandrasekaran and A. L. Baumstark, Magn. Reson. Chem. 31, 489 (1993);
49. (c) D. W. Boykin and A. Kumar, J. Mol. Struct. 298, 121 (1993);
50. (d) A. L. Baumstark and D. W. Boykin, New J. Chem. 16, 357 (1992);
51. (e) D. W. Boykin and A. Kumar, J. Heterocycl. Chem. 29, 1 (1992);
52. (f) D. W. Boykin, A. L. Baumstark and M. Beeson, J. Org. Chem. 56, 1969 (1991);
53. (g) B. Nowak-Wydra, L. W. Allison, A. Kumar and D. W. Boykin, J. Chem. Res. (S) 490 (1991).
54. 18. J.-C. Zhuo, Magn. Reson. Chem. 35, 717 (1997).
55. 19. J.-C. Zhuo, Magn. Reson. Chem. 34, 595 (1996).
56. 20. (a) W. B. Jennings, V. E. Wilson, D. R. Boyd and P. B. Coulter, Org. Magn. Reson. 21, 279 (1983);
57. (b) J. E. Arrowsmith, M. J. Cook and D. J. Hardstone, Org. Magn. Reson. 11, 160 (1978);
58. (c) A. Kawasaki, J. Chem. Soc., Perkin. Trans. 2 223 (1990);
59. (d) R. Akaba, H. Sakuragi and K. Tokumaru, Bull. Chem. Soc. Jpn. 58, 1186 (1985);
60. (e) G. A. Olah and D. J. Donovan, J. Org. Chem. 43, 860 (1978).
61. 21. H.-O Kalinowski, S. Berger and S. Braun, Carbon-13 NMR Spectroscopy, translated by J. K. Becconsall; (a) p. 327; (b) p. 315; (c) p. 342. Wiley, Chichester (1988).
62. 22. C. A. Grobs and H. J. Wilkens, Helv. Chem. Acta 50, 725 (1967).
63. 23. V. A. Petrow, J. Chem. Soc. 693 (1942).
64. 24. (a) J. Bjorgo, D. R. Boyd, C. G. Watson, W. B. Jennings and D. M. Jerina, J. Chem. Soc., Perkin Trans. 2 1081 (1974);
65. (b) A. Padwa, B. Harrison and B. H. Norman, Tetrahedron Lett. 30, 3259 (1989);
66. (c) M. Paventi and A. S. Hay, J. Org. Chem. 56, 5875 (1991).
67. 25. L. P. Vinogradova and S. J. Zav'yalov, Izv. Akad. Nauk SSR, Otd. Khim Nauk 866 (1963); Chem Abstr. 59, 7366f (1963).
68. 25. L. P. Vinogradova and S. J. Zav'yalov, Izv. Akad. Nauk SSR, Otd. Khim Nauk 866 (1963); Chem Abstr. 59, 7366f (1963).
69. 26. U. Kuckländer and H. Töberich, Chem. Ber. 114, 2238 (1981).
70. 27. R. G. Vijay and J. P. Tandon, J. Inorg. Nucl. Chem. 39, 1242 (1977).
71. 28. A. W. Baker and A. T. Shulgin, J. Am. Chem. Soc. 81, 1523 (1959).
72. 29. Breon, US Pat. 2 711 428 (1948).
73. 30. E. B. Knott, J. Chem. Soc. 976 (1947).
74. 31. J. A. Connor D. J. Fine and R. Price, J. Chem. Soc. Dalton Trans. 559 (1981).
75. 32. R. W. Hoffman and K. R. Eichen, Chem. Ber. 102, 2987 (1969).
76. 33. A. Hauser, H. Köppel, T. Forner, K.-D. Schleinitz and H.-G. Henning, J. Prakt. Chem. 319, 263 (1977).