A study of the norcaradiene–cycloheptatriene equilibrium in a series of azulenones by NMR spectroscopy; the impact of substitution on the position of equilibrium
Lorraine M. Bateman(University College Cork), Orla A. McNamara(University College Cork), N. Rachael Buckley(University College Cork), Patrick O’Leary(University College Cork), Francis Harrington(University College Cork), Norma Kelly(University College Cork), Sarah O’Keeffe(University College Cork), Angela Stack(University College Cork), Shane O'Neill(University College Cork), Daniel G. McCarthy(University College Cork), Anita R. Maguire(American Association of Colleges of Pharmacy)
Cited by 23Open Access
Abstract
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.
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