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The search for efficient intramolecular proton transfer from carbon : the kinetically silent intramolecular general base-catalysed elimination reaction of O-phenyl 8-dimethylamino-1-naphthaldoximes.

Asaad, N. and Davies, J. E. and Hodgson, D. R. W. and Kirby, A. J. and Ottavi, L. van Vliet and L. (2005) 'The search for efficient intramolecular proton transfer from carbon : the kinetically silent intramolecular general base-catalysed elimination reaction of O-phenyl 8-dimethylamino-1-naphthaldoximes.', Journal of physical organic chemistry., 18 (2). pp. 101-109.

Abstract

The ready elimination of phenol/phenoxide from the O-phenyl oxime 10E derived from 8-dimethylamino-1-naphthaldehyde, necessarily involving proton transfer from carbon, is catalysed by the neighbouring NMe2 group at pH > 9. However, reaction is faster, rather than slower, at lower pH. It is shown that the step involving proton transfer is not cleanly rate determining at any pH: the preferred route involves syn/anti isomerization to form the more reactive Z-isomer. The rate constant for the anti elimination cannot be extracted from the available data, so no reliable estimate of effective molarity (EM) is possible.

Item Type:Article
Keywords:Proton transfer, Intramolecular general base catalysis, Elimination, Oxime.
Full text:Full text not available from this repository.
Publisher Web site:http://dx.doi.org/10.1002/poc.858
Record Created:12 Apr 2007
Last Modified:08 Apr 2009 16:29

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