Bateman, LM;McNamara, OA;Buckley, NR;O'Leary, P;Harrington, F;Kelly, N;O'Keeffe, S;Stack, A;O'Neill, S;McCarthy, DG;Maguire, AR

2015

January

Organic & Biomolecular Chemistry

A study of the norcaradiene-cycloheptatriene equilibrium in a series of azulenones by NMR spectroscopy; the impact of substitution on the position of equilibrium

Validated

WOS: 15 ()

INTRAMOLECULAR BUCHNER REACTION NUCLEAR-MAGNETIC-RESONANCE METAL-CATALYZED REACTIONS EFFICIENT SYNTHESIS ALPHA-DIAZOKETONES ARYL DIAZOKETONES DIAZO-COMPOUNDS SINGLET OXYGEN CYCLOPROPANATION (+/-)-CONFERTIN

13

11026

11038

A systematic investigation of the influence of substitution at positions C-2 and C-3 on the azulenone skeleton, based on NMR characterisation, is discussed with particular focus on the impact of the steric and electronic characteristics of substituents on the position of the norcaradiene-cycloheptatriene (NCD-CHT) equilibrium. Variable temperature (VT) NMR studies, undertaken to enable the resolution of signals for the equilibrating valence tautomers revealed, in addition, interesting shifts in the equilibrium.

CAMBRIDGE

1477-0520

10.1039/c5ob01346a