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 withα-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.
Similar content being viewed by others
References
V. I. Minkin, L. E. Nivorozhkin, and V. A. Bren, ZhOKh, 35, 1270, 1965.
V. I. Minkin and L. E. Nivorozhkin, ZhOKh, 34, 357, 1964.
L. P. Zalukaev, Izv. AN Latv. SSR, 1, (42), 131, 3 (44), 469, 1951.
V. I. Minkin and Zh. A. Tumakova, ZhOKh, 33, 642, 1963.
V. I. Minkin and L. E. Nivorozhkin, ZhOKh, 34, 2891, 1964.
W. Miller and J. Plochl, Ber., 25, 2021, 1892.
I. A. West, J. Chem. Educ., 40, 194, 1963.
E. H. Suydam, Analyt. Chem., 85, 203, 1963.
M. S. Kharasch, I. Richlin, and F. R. Mayo, J. Am. Chem. Soc., 62, 494, 1940.
V. I. Minkin and M. I. Gorelov, ZhOKh, 33, 647, 1963.
O. A. Osipov and V. I. Minkin, Handbook of Dipole Moments [in Russian], Vysshaya shkola, Moscow, 1965.
L. P. Zalukaev and L. Ya. Spitsina, ZhOKh, 34, 3392, 1964.
C. A. Coulson, Res., 10, 149, 1957.
L. J. Bellamy and J. Williams, Spectrochim. Acta., 9, 341, 1957.
C. P. Smyth, Dielectric Behavior and Structure, N.Y., McGraw-Hill, 1955.
V. I. Minkin and L. E. Nivorozhkin, ZhOrKh, 1, 1632, 1965.
O. A. Osipov, ZhOKh, 26, 322, 1956.
V. I. Minkin, O. A. Osipov, and A. D. Garnovskii, ZhFKh, 36, 469, 1962.
Author information
Authors and Affiliations
Additional information
For communication VI, see [1].
Rights and permissions
About this article
Cite this article
Minkin, V.I., Nivorozhkin, L.E. & Knyazev, A.V. Structure and reactivity of the condensation products of aromatic amines with aliphatic aldehydes. Chem Heterocycl Compd 2, 298–302 (1967). https://doi.org/10.1007/BF00742373
Issue Date:
DOI: https://doi.org/10.1007/BF00742373