A new thiatriazine isomer: Synthesis, tautomerism, and molecular structure of 3,6-diphenyl-4H-1,2,4,5-thiatriazine as a precursor to the 1,2,4,5-thiatriazinyl radical

Journal of Organic Chemistry

Volumn 65, Issue 4, 2000, Pages 931-940

  Farrar, John M ^a   Patel, Mahesh K ^a   Kaszynski, Piotr ^a   Young Jr , Victor G ^b  

^a VANDERBILT UNIVERSITY   (United States)

^b University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LEAD; TRIAZINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; ISOMERISM; OXIDATION; SYNTHESIS; X RAY DIFFRACTION;

EID: 0034712252     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991126l     Document Type: Article

References (51)

1. Kaszynski, P. In Magnetic Properties of Organic Materials; Lahti, P. M., Ed.; Marcel Dekker: New York, 1999; pp 305-324.
2. Patel, M. K.; Huang, J.; Kaszynski, P. Mol. Cryst. Liq. Cryst. 1995, 272, 87.
3. Toyne, K. J. In Thermotropic Liquid Crystals; Gray, G. W., Ed.; Wiley & Sons: New York, 1987; pp 28-63.
4. Demus, D. Mol. Cryst. Liq. Cryst. 1988, 165, 45.
5. Fischer, E. Sulfur Rep. 1992, 11, 257.
6. Fischer, E. In Hetarene IV; Schaumann, E., Ed.; Georg Thieme Verlag: New York, 1998; Vol. E9c, p 803.
7. Boeré, R. T.; Cordes, A. W.; Hayes, P. J.; Oakley, R. T.; Reed, R. W.; Pennington, W. T. Inorg. Chem. 1986, 25, 2445.
8. Butler, R. N.; Evans, A. M.; McNeela, E. M.; O'Halloran, G. A.; O'Shea, P. D.; Cunningham, D.; McArdle, P. J. Chem. Soc., Perkin Trans. 1 1990, 2527.
9. Hassan, A. A.; Ibrahim, Y. R.; Semida, A. A.; Mourad, A.-F. E. Liebigs Ann. Chem. 1994, 989.
10. Spasov, A.; Chemishev, B. Dokl. Bolg. Akad. Nauk 1970, 23, 791; Chem. Abstr. 1970, 73, 120593z.
11. Spasov, A.; Chemishev, B. Dokl. Bolg. Akad. Nauk 1970, 23, 791; Chem. Abstr. 1970, 73, 120593z.
12. Boeré, R. T.; Oakley, R. T.; Reed, R. W.; Westwood, N. P. C. J. Am. Chem. Soc. 1989, 111, 1180.
13. Hayes, P. J.; Oakley, R. T.; Cordes, A. W.; Pennington, W. T. J. Am. Chem. Soc. 1985, 107, 1346.
14. Levchenko, E. S.; Borovikova, G. S.; Borovik, E. I.; Kalinin, V. N. J. Org. Chem. USSR 1984, 20, 176.
15. Markovskii, L. N.; Darmokhval, E. A.; Levchenko, E. S. J. Org. Chem. USSR 1973, 9, 2055.
16. van der Burg, W. J. Recl. Trav. Chim. Pays-Bas 1955, 74, 257.
17. Doyle, K. M.; Kurzer, F. Tetrahedron 1976, 32, 1031.
18. Wolmershäuser, G.; Schnauber, M.; Wilhelm, T. J. Chem. Soc., Chem. Commun. 1984, 573.
19. Kaszynski, P.; Young, V. G., Jr. J. Am. Chem. Soc., in press.
20. Singh, N. K.; Sharma, U. Synth. React. Inorg. Met.-Org. Chem. 1989, 19, 235.
21. Kauffmann, T.; Ban, L.; Kuhlmann, D. Chem. Ber. 1981, 114, 3684.
22. Schulze, B. In Hetarene III; Schaumann, E., Ed.; Georg Thieme Verlag: New York, 1993; Vol. E8a, Part 1, p 668.
23. Dietz, J. In Hetarene III; Schaumann, E., Ed.; Georg Thieme Verlag: New York, 1994; Vol. E8d, Part 4, p 105.
24. Jimonet, P.; Audiau, F.; Barreau, M.; Mignani, S. Heterocycles 1993, 36, 2745.
25. Vasudeva, S. K.; Mahajan, M. P.; Ralhan, N. K. J. Indian Chem. Soc. 1974, 51, 631.
26. Yadav, L. D. S.; Sharma, S. Indian J. Chem., Sect. B 1993, 32, 882 and references therein.
27. Flowers, W. T.; Robinson, J. F.; Taylor, D. R.; Tipping, A. E. J. Chem. Soc., Perkin Trans. 1 1981, 356.
28. Holmberg, B. Ark. Kemi 1956, 9, 65.
29. Evans, D. M.; Taylor, D. R. J. Chem. Soc., Chem. Comunn. 1982, 188.
30. Evans, D. M.; Hill, L.; Taylor, D. R.; Myers, M. J. Chem. Soc., Perkin Trans. 1 1986, 1499.
31. Mayer, K. H.; Lauerer, D. Liebigs Ann. Chem. 1970, 731, 142.
32. Hu, J.; Fox, M. A. J. Org. Chem. 1999, 64, 4959.
33. Steliou, K.; Salama, P.; Corriveau, J. J. Org. Chem. 1985, 50, 4969.
34. Zelenin, K. N.; Khrustalev, V. A.; Sergutina, V. P. J. Org. Chem. USSR 1980, 16, 822.
35. Charles, I.; Latham, D. W. S.; Hartley, D.; Oxford, A. W.; Scopes, D. I. C. J. Chem. Soc., Perkin Trans. 1 1980, 1139.
36. Preliminary results are presented in ref 2.
37. Daley, S. T. A. K.; Rees, C. W.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1984, 57.
38. Sundermeyer, J.; Roesky, H. W.; Noltemeyer, M. Angew. Chem., Int. Ed. Engl. 1989, 28, 609.
39. Pirozhenko, V. V.; Chernega, A. N.; Boldeskul, I. E.; Yufit, D. S.; Antipin, M. Y.; Struchkov, Y. T.; Talanov, V. S.; Shermovich, Y. G. J. Gen. Chem. USSR 1983, 53, 325.
40. Rowland, R. S.; Taylor, R. J. Phys. Chem. 1996, 100, 7384.
41. Miura, Y.; Yamano, E.; Tanaka, A.; Yamauchi, J. J. Org. Chem. 1994, 59, 3294.
42. Markovskii, L. N.; Talanov, V. S.; Polumbrik, O. M.; Shermolovich, Y. G. J. Org. Chem. USSR 1981, 17, 2338.
43. Kornuta, P. P.; Derii, L. I.; Markovskii, L. N. J. Org. Chem. USSR 1980, 16, 1130.
44. Alternatively, the spectrum may be interpreted as a septet if the weak features on the edges of the spectrum are included. This would require three nitrogen atoms with similar hfc's.
45. Kaszynski, P. Submitted for publication.
46. For the purpose of this comparison it has been assumed that the 4H tautomer is the most stable for all isomeric heterocycles. The actual solid-state experimental evidence is available for only three of them.
47. Farrar, J. M.; Huang, J.; Kaszynski, P. Submitted for publication.
48. Gaussian 94, Revision E.1: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A., Gaussian, Inc., Pittsburgh, PA, 1995.
49. Foresman, J. B.; Frisch, A. Exploring Chemistry with Electronic Structure Methods; Gaussian, Inc.: Pittsburgh, PA, 1996.
50. Holmberg, B. Ark. Kemi, Mineral. Geol. 1944, 17A (23), 1.
51. Holmberg, B. Ark. Kemi, Mineral. Geol. 1948, 25A (18), 1.