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Kinetics and mechanism of base catalysed ethyl cyanoformate addition to aldehydes

Lookup NU author(s): Professor Michael North

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Abstract

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.

Publication metadata

Author(s): North M, Urwin S

Publication type: Article

Publication status: Published

Journal: Tetrahedron

Year: 2014

Volume: 70

Issue: 40

Pages: 7100-7105

Print publication date: 07/10/2014

Online publication date: 08/02/2014

Acceptance date: 04/02/2014

ISSN (print): 0040-4020

Publisher: Pergamon Press

URL: http://dx.doi.org/10.1016/j.tet.2014.02.009

DOI: 10.1016/j.tet.2014.02.009

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