Synthesis and structure of N-(4-dialkylaminophenyl)hexafluoro-1,4-naphthoquinone 4-imines

Synthesis and E-Z isomerism of 4-(4-dimethylaminophenylimine) derivatives of 3-dialkylamino-2,5,6,7,8-pentafluoro-1,4-naphthoquinones

“…For all synthesized 3 dialkylami no derivatives 2-8, the F(5) atoms resonate in the range of  31.2-33. 6 for the E isomers and in the range of  19.2-21.6 for the Z isomers. Similar spectral pattern was earlier observed for the low temperature spectrum of the staring compound 1.…”

“…Similar spectral pattern was earlier observed for the low temperature spectrum of the staring compound 1. 6 On going from Z isomer to E iso mer, the signal of the F(5) atom is shifted from  25 to  42, i.e., by 17 ppm. We studied dependence of spectral characteristics of some compounds synthesized on solvent and temperature.…”

“…5 Earlier, we synthesized polyfluorinated 4 aryl 1,4 naphthoquinone imines and found that in solutions the dy namic equilibria between Z and E isomers are shifted to wards the Z isomers. 6 Amination of 2,3,5,6,7,8 hexafluo ro 1,4 naphthoquinone 4 (4 dialkylaminophenylimines) with primary amines led to 3 amino derivatives existing exclusively as the E isomers, which via transformation into the Z isomers underwent subsequent ring closure to give 7 alkyl(aryl) 1,2,3,4,6 pentafluoro 5H benzo[a] phenazin 5 ones. 7 An equilibrium between the Z and E isomers in the series of quinone imines was studied mainly on the exam ple of benzoquinone imines.…”