R. Schoth, E. Lork, G. Röschenthaler
Jun 1, 1996
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0
Influential Citations
8
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Journal
Journal of Fluorine Chemistry
Abstract
Abstract N-(Alkyl)imino derivatives of trifluoroacetyl phenol of the general formula 1,2-C 6 H 4 [C(=NR)CF 3 ] [OH] (R = H, 3a ; Me, 3b; n Pr, 3c ; i Pr, 3d; CH 2 CH 2 NH 2 , 3e ; CH 2 CH 2 CH 2 NH 2 , 3f ; CH 2 CH 2 CH 2 CH 2 NH 2 , 3g ; CH 2 CH 2 OH, 3h ; CH 2 CH 2 NMe 2 , 3i ) were synthesized from 2- trifluoroacetyl phenol and the corresponding primary amines RNH 2 . The molecular structures of 3b [monoclinic, P 2 1 / n , a = 6.641(3), b = 18.044(8), c = 7.716(3) A, β = 99.95(4)°], 3d [orthorhombic, P 2 1 2 1 2 1 , a = 7.784(2), b = 9.291(2), c = 15.942(4) A] and 3i [mono- clinic, P 2 1 / n , a = 8.660(2), b = 18.135(2), c = 13.300(2) A, β = 99.83 (2)°] were determined. In the solid state, 3b, 3d and 3i exist exclusively as E isomers with inter molecular hydrogen bridges, whereas according to the 1 H and 19 F NMR spectra in chloroform solution, compounds 3b, 3c and 3d isomerize to give a mixture of 66% Z and 34% E isomers.