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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.H. Atherton

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