High nitrogen chemistry: Synthesis and properties of N,N-bis(4,5- dicyano-1-methyl-2-imidazolyl)cyanamide and N,N,N',N',N'',N''-hexakis(4,5- dicyano-1-methyl-2-imidazolyl) melamine

Tetrahedron

Volumn 55, Issue 2, 1999, Pages 353-358

  Subrayan, Ramachandran P ^a,b   Rasmussen, Paul G ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

^b King Industries Incorporated   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYANAMIDE; N,N BIS(4,5 DICYANO 1 METHYL 2 IMIDAZOLYL)CYANOMIDE; N,N,N',N',N'',N'' HEXAKIS(4,5 DICYANO 1 METHYL 2 IMIDAZOLYL)MELAMINE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; FLUORESCENCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTROFLUOROMETRY; STEREOCHEMISTRY; SYNTHESIS; THERMOSTABILITY;

EID: 0033534608     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01058-8     Document Type: Article

References (40)

1. a) Subrayan, R. P.; Rasmussen, P. G. Trends Polym. Sci. 1995, 3, 165.
2. b) Yacaman, M. J.; Gil, J. M.; Gil, F. J.; Sarikaya, M.; Qian, M. X. Mater. Chem. Phys. 1997, 47, 109.
3. c) Sundgren, J. -E. NATO ASI Ser., Ser. 3, 1997, 21 (Protective Coatings and Thin Films), 335.
4. d) Teter, D. M.; Hemley, R. J. Science 1996, 271, 53.
5. e) Stevens, A. J.; Koga, T.; Agee, C. B.; Aziz, M. J.; Lieber, C. M. J. Am. Chem. Soc. 1996, 118, 10900.
6. Apen, P. G.; Rasmussen, P. G. Heterocycles 1989, 29, 1325.
7. Apen, P. G.; Rasmussen, P. G. J. Am. Chem. Soc. 1991, 113, 6178.
8. Coad, E. C.; Apen, P. G.; Rasmussen, P. G. J. Am. Chem. Soc. 1994, 116, 391.
9. Subrayan, R. P.; Kampf, J. W.; Francis, A. H.; Rasmussen, P. G. Chem. Mater. 1995, 7, 2213.
10. Subrayan, R. P.; Kampf, J. W.; Rasmussen, P. G. J. Org. Chem. 1994, 59, 4341.
11. a) Subrayan, R. P., Ph.D. Thesis, The University of Michigan, Ann Arbor, 1993.
12. b) Jang, T., Ph.D. Thesis, The University of Michigan, Ann Arbor, 1996.
13. Subrayan, R. P.; Rasmussen, P. G. Tetrahedron 1995, 51, 6167.
14. For selected examples see a) Lin, S. -C.; Pearce, E. M. High-Performance Thermosets: Chemistry, Properties, Applications, Hanser Publishers, New York, 1994, pp. 65-108.
15. b) Patel, B. K. in Kirk-Othmer Encyclopedia of Chemical Technology, Kroschwitz, J. I.; Howe-Grant, M., Eds., Fourth Edition, John Wiley & Sons, New York, 1993, 7, pp. 748-750.
16. c) Korshak, V. V.; Vasnev, V. A. in Comprehensive Polymer Science, Allen, G.; Bevington, J. C., Eds, Pergamon Press, New York, 1989, 5, pp. 131-142.
17. a) Lindeman, S. V.; Shklover, V. E.; Struchkov, Yu. T.; Kuznetsov, S. N.; Pamkratov, V. A. Kristallografiya 1982, 27, 65; Sov. Phys. Crystallogr. 1982, 27, 36.
18. a) Lindeman, S. V.; Shklover, V. E.; Struchkov, Yu. T.; Kuznetsov, S. N.; Pamkratov, V. A. Kristallografiya 1982, 27, 65; Sov. Phys. Crystallogr. 1982, 27, 36.
19. b) Domalski, E. S.; Hearing, E. D. J. Phys. Chem. Ref. Data 1990, 19, 881.
20. a) Fukushima, Y.; Nohara, N.; Hashida, Y.; Sekiguchi, S.; Matsui, K. Bull. Chem. Soc. Jpn. 1971, 44, 794.
21. b) Nohara, N.; Sekiguchi, S.; Matsui, K. J. Heterocyclic Chem. 1970, 7, 519.
22. Kawaguchi, M.; Nozaki, K. Chem. Mater. 1995, 7, 257.
23. Kim, C.; Chang, Y.; Kim, J. S. Macromolecules 1996, 29, 6353.
24. Purdy, A. P.; Houser, E.; George, C. F. Polyhedron 1997, 16, 3671.
25. Madelung, W.; Kern, E. Ann. Chem. 1922, 427, 26.
26. Stickley, K. R.; Blackstock, S. C. Tetrahedron Lett. 1995, 36, 1585.
27. a) Ishikawa, W.; Noguchi, K.; Kuwabura, Y.; Shirota, Y. Adv. Mater. 1993, 5, 559.
28. b) Ishikawa, W.; Inada, H.; Nakano, H.; Shirota, Y. Chem. Lett. 1991, 1731.
29. c) Inada, H.; Shirota, Y. J. Mater. Chem. 1993, 3, 319.
30. d) Shirota, Y.; Kobata, T.; Noma, N. Chem. Lett. 1989, 1145.
31. e) Higuchi, A.; Inada, H.; Kobata, T.; Shirota, Y. Adv. Mater. 1991, 3, 549.
32. Johannsen, I.; Torrance, J. B.; Nazzal, A. Macromolecules 1989, 22, 566.
33. Sander, R.; Stümpflen, V.; Wendroff, J. H.; Greiner, A. Macromolecules 1996, 29, 7708.
34. For examples see a) Wang, D. W.; Fisher, M. M. J. Polym. Sci.: Polym. Chem. Ed. 1983, 21, 671.
35. b) Desai, N. V.; Desai, K. R. Eur. Polym. J. 1992, 28, 435.
36. c) Shah, P. P. J. Macromol. Sci.-Chem. 1984, A21, 715.
37. d) Mikroyannidis, J. A. J. Polym. Sci: Part A: Polym. Chem. 1988, 26, 583.
38. e) Audbert, R.; Néel, J. J. Polym. Sci.: Part C 1968, 3245.
39. f) Costa, L.; Camino, G.; Martnasso, G. Polym. Prepr., Am. Chem. Soc., Div. Polym. Chem. 1986, 30(1), 531.
40. Bollaert, V.; De Schryver, F. C.; Tackx, P.; Persoons, A.; Nussler, J. J. H.; Put, J. Adv. Mater. 1993, 5, 268.