158759-41-2Relevant academic research and scientific papers
(Z,Z)-5-Anilino-1,1,1,6,6,6-hexafluoro-3,4-diazahexa-2,4-diene-2-amine
Abdul-Ghani, Mohamad,Beagley, Brian,Pritchard, Robin G.,Tipping, Anthony E.
, p. 1492 - 1494 (1994)
The title molecule, C10H8F6N4, has been characterized crystallographically, thus establishing its isomeric form.This form has a C==N--N==C substructure with a torsion angle of 145(1) deg about the N--N bond.There is an extensive hydrogen-bonding system, s
Unsaturated nitrogen compounds containing fluorine. Part 16. The synthesis of 3,5-bis(trifluoromethyl)-1H-1,2,4- triazole and some 4-substituted derivatives from 2,5-dichloro-1,1,1,6,6,6-hexafluoro-3,4-diazahexa-2,4-diene
Abdul-Ghani, Mohammad M.,Tipping, Anthony E.
, p. 95 - 106 (2007/10/02)
The dichloroazine 5 has been converted into the monoaminoazines CF3C(NHR)=NN=CClCF3 (6) and the diaminoazines CF3C(NHR)=NN=C(NHR)CF3 (4) by reaction with ammonia or the appropriate primary amino compound; with hydroxylamine the syn-oxime CF3CCl=NNHC(CF3)=NOH (8) (86percent) was formed.The mixed diaminoazines CF3C(NHR)=NN=C(NHR')CF3 (4) have been synthesised from the monoaminoazines 6a-d.A solution of the diaminoazine 4c, heated in ethanol under reflux, gave 3,5-bis(trifluoromethyl)-1H-1,2,4-triazole (1a) (28percent) and its ammonium salt NH4+- (7b) (54percent), while the azines 4g and 4j under the same conditions each afforded 4-phenyl-3,5-bis(trifluoromethyl)-4H-1,2,4-triazole (2c) (ca. 85percent).Thermolysis of the diaminoazines 4c-f and 4h in vacuo over the range 120-150 deg C gave the following results: 4c--->7b (98percent); 4d--->MeNH3+- (7c) (ca. 26percent) + Me4N+- (7d) (ca.13percent) + 4-methyl-3,5-bis(trifluoromethyl)-4H-1,2,4-triazole (2b) (54percent) + 1-methyl-3,5-bis(trifluoromethyl)-1H-1,2,4-triazole (1b) (1.5percent); 4e---> the 4-carbomethoxymethyltriazole (2e) (93percent); 4f---> the 4-carboethoxymethyltriazole (2f) (82percent); 4h--->1a (11percent) + 2b (54percent) + 7c (31percent).Treatment of salt 7b with aqueous hydrochloric acid afforded the triazole 1a (75percent). - Keywords: Unsaturated nitrogen compounds; Synthesis; Bis(trifluoromethyl)triazole; NMR spectroscopy; Mass spectrometry
