Structure and reactivity of the condensation products of aromatic amines with aliphatic aldehydes |
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Authors: | V. I. Minkin L. E. Nivorozhkin A. V. Knyazev |
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Affiliation: | (1) Rostov-on-Don State University, USSR |
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Abstract: | A number of previously undescribed propylidenearylamine dimers have been synthesized by the interaction of propionaldehyde with a series of para-substituted anilines(R=H, CH3, OCH3, F, Cl, Br, I) and with-naphthylamine. The structure of the bis-propylidenearylamines has been established by a study of their IR and UV spectra. It has been shown that all the bis-propylidenearylamines, except for bis(propylidene-p-fluoroaniline), have the structure of 2-ethyl-3-methyl-4-arylamino-1, 2, 3, 4-tetrahydroquinolines. The dipole moments of the bis(propylidene-p-R-anilines) have been determined. Comparison of the values obtained with the calculated values indicates that the most favorable molecular conformation of the bispropylidenearylamines is a tetrahydroquinoline half-chain with quasi-equatorial positions for the 4-NHAr and NH groups and an equatorial 3-CH3 group. In contrast to the bis-ethylideneanilines, we did not succeed in finding other stable conformers for the bis-propylidene derivatives. It has been established that bis (propylidene-p-fluoroaniline) has the 1, 3-bis (p-fluorophenylamino)-2-ethyl-1-hexene structure.For communication VI, see [1]. |
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