A study of the norcaradiene-cycloheptatriene equilibrium in a series of azulenones by NMR spectroscopy; the impact of substitution on the position of equilibrium
Bateman, Lorraine M.; McNamara, Orla A.; Buckley, N. Rachael; O'Leary, Patrick; Harrington, Francis; Kelly, Norma; O'Keeffe, Sarah; Stack, Angela; O'Neill, Shane T.; McCarthy, Daniel G.; Maguire, Anita R.
Date:
2015-09-08
Copyright:
© 2015, the Authors. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Citation:
BATEMAN, L. M., MCNAMARA, O. A., BUCKLEY, N. R., O'LEARY, P., HARRINGTON, F., KELLY, N., O'KEEFFE, S., STACK, A., O'NEILL, S., MCCARTHY, D. G. & MAGUIRE, A. R. 2015. A study of the norcaradiene-cycloheptatriene equilibrium in a series of azulenones by NMR spectroscopy; the impact of substitution on the position of equilibrium. Organic & Biomolecular Chemistry, 13, 11026-11038. http://dx.doi.org/10.1039/C5OB01346A
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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Except where otherwise noted, this item's license is described as © 2015, the Authors. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.