13715-55-4Relevant academic research and scientific papers
Investigations on Diazo Compounds and Azides, LII: Stable Azomethine Imine Dipoles from Diazo Compounds and 3H-1,2,4-Triazole-3,5(4H)-diones
Theis, Wolfgang,Bethaeuser, Willi,Regitz, Manfred
, p. 28 - 41 (2007/10/02)
The aryl-substituted diazo compounds 1a-h react with the triazolediones 2a-c at 20 deg C in benzene with loss of nitrogen to the stable azomethine imine dipoles 4a-p.Their 1,3-dipolar character is revealed in the addition of methanol and ethanol (4d-f -> 5a-f) as well as in cycloaddition reactions with dimethyl acetylenedicarboxylate (4d,e -> 6a,b) and phenyl isocyanate (4d -> 7).Bisdipoles are obtained by two different ways: Either bisdiazo compounds are reacted with 4-phenyl-3H-1,2,4-triazole-3,5(4H)-dione (12a,b + 2 2a -> 13a,b) or the bistriazoledione 14 is transformed into the bisdipoles 15a-d with diazo compounds (1a,c,d, and i).Dipole moments, molecular weights, IR, UV, 1H NMR, and 13C NMR spectroscopic data are in agreement with the dipole structures.
