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Effect of perfluoroalkyl substituents onthe formation and costitutional dynamics of Schiff bases
Štrympl, Ondřej ; Vohlídal, Jiří (advisor) ; Jindřich, Jindřich (referee)
New synthetic routes were designed and applied for novel bisperfluoroalkylated benzene derivatives: 2,5-bis(perfluorooctyl)benzene-1,4-dicarbaldehyde, its dimethylacetal and 2,5- bis(trifluoromethyl)benzene-1,4-diamine. Methods for purification of those derivatives were developed and used to obtain pure crystalline compounds. Crystals of the mentioned diamine and diacetal were obtained in quality suitable for RTG analysis while crystals of dialdehyde were of sufficient quality. New synthesis and purification protocol was designed for 2,5-bis(trifluoromethyl)benzene- 1,4-dialdehyde yielding sufficiently pure product, although isolated amounts are rather small ( yields about 20%) . 2,5-diiodobenzene-1,4-diamine was synthetised. It should be possible to prepare 2,5- bis(perfluorooktyl)benzene-1,4-diamine from this compound either by direct or indirect approach. Nevertheless, the syntheses were yet unsuccessful. A series of eight Schiff bases derived from 3,5-bistrifluoromethylated benzeneamine, benzylamine and benzaldehyde, and three reference bases based on thiophene-2-carbadehyde, benzaldehyde and phenylacetaldehyde was prepared. Kinetics of those species' formation in CDCl3 (all reactions run without catalyst) and THF (necessity of catalysis and susceptibility of equilibria to water) were studied. The...
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