J.H. Atherton
The Strecker reaction: kinetic and equilibrium studies of cyanide addition to iminium ions
Atherton, J.H.; Blacker, J.; Crampton, M.R.; Grosjean, C.
Authors
J. Blacker
M.R. Crampton
C. Grosjean
Abstract
Kinetics studies are reported of the reactions of benzylidene benzylamine, 4a, and of benzylidene allylamine, 4b, with cyanide in aqueous buffers to give the corresponding a-aminonitriles. The results allow the calculation of values of rate and equilibrium constants for reaction of the iminium ions formed from 4a and 4b with cyanide ions. These values are compared with those, obtained from the hydrolysis reactions, for reaction of the iminium ions with hydroxide ions and with water. Comparison with some other iminium ions reveals that those formed from 4a and 4b are relatively unreactive due to the possibilities of charge delocalisation.
Citation
Atherton, J., Blacker, J., Crampton, M., & Grosjean, C. (2004). The Strecker reaction: kinetic and equilibrium studies of cyanide addition to iminium ions. Organic and Biomolecular Chemistry, 2(18), 2567-2571. https://doi.org/10.1039/b407853e
Journal Article Type | Article |
---|---|
Publication Date | 2004-08 |
Deposit Date | Apr 20, 2007 |
Journal | Organic and Biomolecular Chemistry |
Print ISSN | 1477-0520 |
Electronic ISSN | 1477-0539 |
Publisher | Royal Society of Chemistry |
Peer Reviewed | Peer Reviewed |
Volume | 2 |
Issue | 18 |
Pages | 2567-2571 |
DOI | https://doi.org/10.1039/b407853e |
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