113934-49-9Relevant academic research and scientific papers
ACYLOTROPIC TAUTOMERISM. XXIV. DEGENERATE CARBONOTROPY IN THE O-IMIDOYL DERIVATIVES OF TROPOLONE. PERMUTATION ANALYSIS OF THE MECHANISMS OF TAUTOMERISM AND STEREODYNAMICS
Olekhnovich, L. P.,Kurbatov, S. V.,Borisenko, N. I.,Budarina, Z. N.,Minkin, V. I.,Zhdanov, Yu. A.
, p. 1614 - 1624 (2007/10/02)
Reversible migration of the imidoyl groups (k298K = 1E-1 - 5E3 sec-1) between the O atoms of 3,5,7-trimethyltropolone, accompanied by the two stereodynamic processes of Z E inversion of the migrant and syn-anti (s a) conformational isomerization of the 2-imidoyloxytropones (k298K = 3E1 - 3E4 sec-1), were detected by dynamic (1)H NMR spectroscopy in the series of O-(N-phenyl)benzimidoyl derivatives of tropolones, which were synthesized for the first time.As a result of permutation analysis and computer modeling of the dynamic NMR spectra the mechanism of imidoylotropy was defined as a suprafacial -sigmatropic shift, taking place with retention of the Z or E configuration of the migrant and its s or a orientation in relation to the tropolone system.
