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Issue 18, 2004
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The Strecker reaction: kinetic and equilibrium studies of cyanide addition to iminium ions

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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 α-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.

Graphical abstract: The Strecker reaction: kinetic and equilibrium studies of cyanide addition to iminium ions

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Publication details

The article was received on 26 May 2004, accepted on 23 Jul 2004 and first published on 24 Aug 2004


Article type: Paper
DOI: 10.1039/B407853E
Citation: Org. Biomol. Chem., 2004,2, 2567-2571
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    The Strecker reaction: kinetic and equilibrium studies of cyanide addition to iminium ions

    J. H. Atherton, J. Blacker, M. R. Crampton and C. Grosjean, Org. Biomol. Chem., 2004, 2, 2567
    DOI: 10.1039/B407853E

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