Stereodynamics of 1-(methylsulfonyl)-3,5-bis(trifluoromethylsulfonyl)-1,3, 5-triazinane: Experimental and theoretical analysis

Journal of Organic Chemistry

Volumn 71, Issue 20, 2006, Pages 7638-7642

  Shainyan, Bagrat A ^a   Ushakov, Igor A ^a   Koch, Andreas ^b   Kleinpeter, Erich ^b  

^a A E FAVORSKY IRKUTSK INSTITUTE OF CHEMISTRY   (Russian Federation)

^b UNIVERSITY OF POTSDAM   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; CONFORMATIONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION KINETICS; STEREOCHEMISTRY;

PERLIN EFFECTS; RING INVERSION; STEREODYNAMICS;

PARAFFINS;

1 (METHYLSULFONYL) 3,5 BIS(TRIFLUOROMETHYLSULFONYL) 1,3,5 TRIAZINANE; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CONFORMATION; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; TEMPERATURE DEPENDENCE;

EID: 33749123457     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061112x     Document Type: Article

References (28)

1. (a) Bushweller, C. H. In Conformational Behavior of Six-Membered Rings. Analysis, Dynamics, and Stereoelectronic Effects; Juaristi, E., Ed.; VCH Publishers: New York, 1995.
2. (b) Kleinpeter, E. Adv. Heterocycl. Chem. 2004, 86, 41-127.
3. (a) Roux, M. V.; Jimenez, P.; Davalos, J. Z.; Notario, R.; Juaristi, E. J. Org. Chem. 2001, 66, 5343-5351.
4. (b) Alabugin, I. V. J. Org. Chem. 2000, 65, 3910-3919.
5. (c) Alabugin, I. V.; Manoharan, M. J. Org. Chem. 2004, 69, 9011-9024.
6. (d) Freeman, F.; Derek, E. J. Comput. Chem. 2003, 24, 909-919.
7. (d) Shainyan, B. A.; Ushakov, I. A.; Suslova, E. N. J. Sulfur Chem. 2006, 27, 3-13.
8. (a) Kleinpeter, E.; Taddei, F.; Wacker, P. Chem. - Eur. J. 2003, 9, 1360-1368.
9. (b) Kleinpeter, E.; Koch, A.; Pihlaja, K. Tetrahedron 2005, 61, 7349-7358.
10. (c) Freeman, F.; Cha, C.; Fang, C.; Huang, F. C.; Hwang, J. H.; Louie, P. L.; Shainyan, B. A. J. Phys. Org. Chem. 2005, 18, 35-48.
11. (d) Freeman, F.; Asgari, N.; Entezam, B.; Gomarooni, F.; Mac, J.; Nguyen, M. H.; Nguyen, N. N. T.; Nguyen, T. P.; Pham, N. B.; Sultana, P.; Welch, T. S.; Shainyan, B. A. Int. J. Quantum Chem. 2005, 101, 40-54.
12. (e) Freeman, F.; Entezam, B.; Gomarooni, F.; Welch, T. S.; Shainyan, B. A. J. Organomet. Chem. 2005, 690, 4103-4113.
13. (f) Freeman, F.; Shainyan, B. A. Int. J. Quantum Chem. 2005, 105, 313-324.
14. (g) Shainyan, B. A. Int. J. Quantum Chem. 2006, in press.
15. Shainyan, B. A.; Kirpichenko, S. V. Russ. J. Gen. Chem. (Engl. Transl.) 2003, 73, 1709-1714.
16. Jewett, J. G.; Breeyear, J. J.; Brown, J. H.; Bushweller, C. H. J. Am. Chem. Soc. 2000, 122, 308-323.
17. Anderson, J. E.; Casarini, D.; Ijeh, A. I.; Lunazzi, L.; Tocher, D. A. J. Am. Chem. Soc. 1995, 117, 3054-3056.
18. Mescheryakov, V. I.; Albanov, A. I.; Shainyan, B. A. Russ. J. Org. Chem. (Engl. Transl.), 2005, 41, 1381-1386.
19. Shainyan, B. A.; Mescheryakov, V. I.; Albanov, A. I.; Sigalov, M. V. Tetrahedron Lett. 2005, 46, 6199-6201.
20. Bax, A.; Subramanian, S. J. Magn. Reson. 1986, 67, 565-569.
21. (a) Lyapkalo, I. M.; Reissig, H.-U.; Schäefer, A.; Wagner, A. Helv. Chim. Acta 2002, 85, 4206-4215.
22. Cuevas, G.; Juaristi, E. J. Am. Chem. Soc. 2002, 124, 13088-13096.
23. Cuevas, G.; Martínez-Mayorga, K.; Fernández-Alonso, M. C.; Jiménez-Barbero, J.; Perrin, C. L.; Juaristi, E.; López-Mora, N. Angew. Chem., Int. Ed. 2005, 44, 2360-2364.
24. Perrin, C. L.; Erdélyi, M. J. Am. Chem. Soc. 2005, 127, 6168-6169.
25. Shainyan, B. A.; Ushakov, I. A.; Suslova, E. N. J. Sulfur Chem. 2006, 27, 3-13.
26. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision B.03; Gaussian, Inc.: Pittsburgh, PA, 2003.
27. Ditchfield, R. J. Chem. Phys. 1972, 56, 5688-5691.
28. Wolinski, K.; Hinton, J. F.; Pulay, P. J. Am. Chem. Soc. 1990, 112, 8251-8260.