134785-07-2Relevant academic research and scientific papers
ACYLOTROPIC TAUTOMERISM. XXXI. TORSIONAL STEREODYNAMICS OF THE N-HETEROARYL DERIVATIVES OF 2-AMINOTROPONES
Olekhnovich, L. P.,Kurbatov, S. V.,Lesin, A. V.,Budarina, Z. N.,Zhdanov, Yu. A.,Minkin, V. I.
, p. 4 - 10 (2007/10/02)
N-3,5-Dinitropyridyl and 4,6-dichloro-1,3,5-triazinyl derivatives of 2-aminotropones with prochiral substituents (isopropyl, benzyl) at the nitrogen center were synthesized.It was found by NMR spectroscopy that unlike the model 2-dibenzylaminotropone the heteroarylaminotropones have the acoplanar chiral configuration in solutions with the ''flagstaff'' arrangement of the heteroaryl in relation to the tropone.At normal temperatures degenerate configurational isomerism with k298 ca. 8*103 - 5*104 sec-1 achieved by correlated torsional rotations about the N-C bonds is realized.It was established that the direction and sign of the torsional rotations depend on the symmetry (C2v) or asymmetry (Cs) in the structure of the heteroaryl fragment.
