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The mechanism by which tertiary amines catalyse the formation of cyanohydrin carbonates from aldehydes and alkyl cyanoformates is investigated by means of a kinetic study. The reaction rate shows a second order dependence on amine concentration unless the amine is sterically hindered, when the rate has a first order dependence on amine concentration. The catalytic activity of the amine correlated with its pK(aH). On the basis of these results, a mechanism is proposed in which the amine acts as a base to activate a water molecule, which reacts with the ethyl cyanoformate generating cyanide in situ. (C) 2014 Elsevier Ltd. All rights reserved.
Author(s): North M, Urwin S
Publication type: Article
Publication status: Published
Print publication date: 07/10/2014
Online publication date: 08/02/2014
Acceptance date: 04/02/2014
ISSN (print): 0040-4020
Publisher: Pergamon Press
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