Christophe Grosjean - The Strecker reaction: kinetic and equilibrium studies of cyanide addition to iminium ions

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  Publication Details (including relevant citation   information):

  Atherton, J. H.; Blacker, J,; Crampton, M. R.; Grosjean, C.   Org. Biomol. Chem., 2004, 2,   2567‐2571


  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.

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