124980-85-4Relevant articles and documents
TAUTOMERISM AND STEREODYNAMICS OF INDOPHENOLS AND AMIDINES AND THEIR DERIVATIVES AND ANALOGS. I. EFFECT OF INTRAMOLECULAR HYDROGEN BONDING ON THE KINETICS AND MECHANISM OF ZE ISOMERISATION OF ortho-INDOPHENOLS
Lyubchenko, S. N.,Ivakhchenko, E. P.,Ryskina, T. A.,Prokof'ev, A. I.,Kogan, V. A.,Olekhnovich, L. P.
, p. 975 - 982 (2007/10/02)
1.The actual mechanism for the ZE isomerization of ortho-indophenols involves planar inversion of configuration at the C=N bond.The rates of this process range from 1E-6 to 1E-7 sec-1 and increase to 1E11 sec-1 upon the conversion of the ortho-indophenols to paramagnetic forms (at 298 K). 2.The existence of intramolecular hydrogen bonding in ortho-indophenols leads to hydrogen bond dissociation and formation and torsional twisting of the phenol fragment concerted with planar inversion at the C=N bond. 3.The stereodynamics of para-indophenols is a function of intermolecular proton exchange.ZE isomerization by a torsional twisting mechanism is possible only by blocking the p-electron pair of the imine nitrogen by N-methylation.