SYNTHESIS, CHARACTERIZATION, AND THERMOLYSIS OF C15N12

Citation
Ec. Coad et al., SYNTHESIS, CHARACTERIZATION, AND THERMOLYSIS OF C15N12, Journal of organic chemistry, 61(19), 1996, pp. 6666-6672
Citations number
40
Categorie Soggetti
Chemistry Inorganic & Nuclear
ISSN journal
00223263
Volume
61
Issue
19
Year of publication
1996
Pages
6666 - 6672
Database
ISI
SICI code
0022-3263(1996)61:19<6666:SCATOC>2.0.ZU;2-M
Abstract
Synthesis of 1-methyl-2-fluoro-4,5-dicyanoimidazole was done by haloge n exchange between 1-methyl-2-bromo-4,5-dicyanoimidazole and potassium fluoride. Halogen exchange between 1-methyl-2-bromo-4,5-dicyanoimidaz ole and lithium chloride in N-methylpyrrolidinone at 150 degrees C yie lded 1-methyl-2-chloro-4,5-dicyanoimidazole, and additional heating to 210 degrees C resulted in the demethylation to yield 2-chloro-4,5-dic yanoimidazole. Thermolyses of the 2-halo-4,5-dicyanoimidazole derivati ves (F, Cl) and 1-iodo-2-halo-4,5-dicyanoimidazole derivatives (Cl, Br , I) between 100 and 290 degrees C were found to yield ,2-e]-1,3,5-tri azine-2,3,5,6,8,9-hexacarbonitrile, or HTT, with (C5N4)(3) composition . HTT has been characterized and purified and the crystal structure ob tained. Thermolysis of HTT at 490-500 degrees C gives a material with C/N = 1.020. The thermal properties of HTT and its decomposition produ cts show thermal stability to 350 degrees C.