Conformational Studies by Dynamic NMR. 63.1 Stereodynamics of Dialkylamino Ethoxy Bisulfides: S-S and S-N Rotation Processes

Journal of Organic Chemistry

Volumn 63, Issue 12, 1998, Pages 3933-3936

  Cerioni, G ^a   Cremonini, M A ^b   Lunazzi, L ^c   Placucci, G ^c   Plumitallo, A ^a  

^a UNIVERSITY OF CAGLIARI   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

^c UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0006073597     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo972259e     Document Type: Article

References (47)

1. For Part 62 see: Casarini, D.; Lunazzi, L.; Mazzanti, A. J. Org. Chem. 1997, 62, 7592.
2. Kessler, H.; Rundel, W. Chem. Ber. 1968, 101, 3350.
3. Kessler, H.; Rieker, A.; Rundel, W. J. Chem. Soc., Chem. Commun. 1968, 475.
4. Bushweller, C. H. Int. J. Sulfur Chem. 1973, 8, 103.
5. Pinto, B. M.; Leung, R. Y. N.; Sharma, R. D. Magn. Reson. Chem. 1988, 26, 729.
6. Fraser, R. R.; Boussard, G.; Saunders: J. K.; Lambert, J. B. Mixan, C. E. J. Am. Chem. Soc. 1971, 93, 3822.
7. Rauk, A. J. Am. Chem. Soc. 1984, 106, 6517.
8. (a) Lee, J. D.; Bryant, M. W. R. Acta Crystallogr. 1969, B25, 2094.
9. (b) Sacerdoti, M.; Gilli, G.; Marsh, E. Acta Crystallogr. 1975, B31, 327.
10. Steudel, R.; Drozdova, Y.; Miaskiewicz, K.; Hertwig, R. H.; Koch, W. J. Am. Chem. Soc. 1997, 119, 1990.
11. Kost, D.; Raban, M.J. Am. Chem. Soc. 1982, 104, 2960.
12. (a) Raban, M.; Kost, D. J. Am. Chem. Soc. 1972, 94, 3234.
13. (b) Kost, D.; Egozy, H. J. Org. Chem. 1989, 54, 4909.
14. (c) Raban, M.; Noyd, D. A.; Bermann, L. J. Org. Chem. 1975, 40, 752.
15. (d) Raban, M.; Kost, D. In Acyclic Organonitrogen Stereodynamics; Lambert, J. B., Takeuchi, Y., Eds.; VCH Publishers: New York, 1992; Chapter 2, p 71.
16. (e) Raban, M.; Kenney, G. W. J., Jr.; Jones, F. B., Jr. J. Am. Chem. Soc. 1969, 91, 6677.
17. (a) Bingham, R. C. J. Am. Chem. Soc. 1975, 97, 6743.
18. (b) Pinto, B. M. In Acyclic Organonitrogen Stereodynamics; Lambert, J. B., Takeuchi, Y., Eds.; VCH Publishers: New York, 1992; Chapter 5, p 149.
19. Burdon, J.; Hotchkiss, J. C.; Jennings, W. B. J. Chem. Soc. Perkin Trans. 2 1976, 1052.
20. (a) Koritsanszky, T.; Buschmann, J.; Luger, P.; Schmidt, H.; Steudel, R. J. Phys. Chem. 1994, 98, 5416.
21. (b) Steudel, R.; Schmidt, H.; Baumeister, E.; Oberhammer, H.; Koritsanszky, T. J. Phys. Chem. 1995, 99 , 8987.
22. Borghi, R.; Lunazzi, L.; Placucci, G.; Cerioni, G.; Foresti, E.; Plumitallo, A. J. Org. Chem. 1997, 62, 4924.
23. Seel, F.; Gombler, W.; Budenz, R. Liebigs Ann. Chem. 1970, 725, 1.
24. (a) Epiotis, N. D.; Cherry, W. R.; Shaik, S.; Yates, R. L.; Bernardi, F. Topics in Current Chemistry: Structural Theory of Organic Chemistry; Springer-Verlag: Berlin, 1977; Vol. 70.
25. (b) Cieplak, A. S. J. Am. Chem. Soc. 1981, 103, 4540.
26. (a) Jørgensen, F. S.; Snyder, J. P. Tetrahedron 1979, 35, 1399.
27. (b) Cardenas-Jiron, G. I.; Cárdenas-Lailhacar, C.; Toro-Labbé, A. J. Mol. Struct (THEOCHEM) 1993, 282, 113.
28. (c) Samdal, S.; Mastryukov, V. S.; Boggs, J. E. J. Mol. Struct (THEOCHEM) 1994, 309, 21.
29. (a) Forsyth, D. A.; Johnson, S. M. J. Am. Chem. Soc. 1994, 116, 11481.
30. (b) Anderson, J. E.; Casarini, D.; Ijeh, A. I.; Lunazzi, L. J. Am. Chem. Soc. 1997, 119, 8050.
31. Casarini, D.; Davalli, S.; Lunazzi, L.; Macciantelli, D. J. Org. Chem. 1989, 54, 4616.
32. Lehn, J. M.; Wagner, J. J. Chem. Soc., Chem. Commun. 1968, 1298.
33. (a) Raban, M.; Jones, F. B., Jr.; Kenney, G. W. J., Jr. Tetrahedron Lett. 1968, 5055.
34. (b) Raban, M.; Kenney, G. W. J., Jr. Tetrahedron Lett. 1969, 1295.
35. Drakenberg, T.; Lehn, J. M. J. Chem. Soc., Perkin Trans. 2 1972, 532.
36. Cowley, A. H.; Dewar, M. J. S.; Jackson, W. R. J. Am. Chem. Soc. 1968, 90, 4185.
37. Lambert, J. B. Topics Stereochem. 1971, 6, 19.
38. Jackson, W. R.; Kee, T. G.; Jennings, W. B. Tetrahedron Lett. 1974, 1839.
39. Bushweller, C. H.; Laurenzi, B. J.; Brennan, J. G.; Goldberg, M. J.; Marcantonio, R. P. In Stereodynamics of Molecular Systems; Sarma, R., Ed.; Pergamon Press: New York, 1979; p 113.
40. Lunazzi, L.; Macciantelli, D.; Grossi, L. Tetrahedron 1983, 39, 305.
41. i) as models for 1, 2, and 3, respectively. In the case of 1 we checked that the results were not affected by the substitution of the EtO with the MeO group.
42. (a) Casarini, D.; Lunazzi, L.; Anderson, J. E. J. Org. Chem. 1993, 58, 714.
43. (b) Anderson, J. E.; Casarini, D.; Lunazzi, L. J. Org. Chem. 1996, 61, 1290.
44. Bock, H.; Goebel, I.; Havlas, Z.; Liedle, S.; Oberhammer, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 187.
45. Borghi, R.; Lunazzi, L.; Placucci, G.; Cerioni, G.; Plumitallo, A. J. Org. Chem. 1996, 61, 3327.
46. Kagami, H.; Motoki, S. J. Org. Chem. 1977, 42, 4139.
47. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. J.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. J. Comput. Chem. 1993, 14, 1347.