Kinetics and mechanism of base catalysed ethyl cyanoformate addition to aldehydes |
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Authors: | Michael North Stephanie Urwin |
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Institution: | 1. Green Chemistry Centre of Excellence, Department of Chemistry, The University of York, Heslington, York YO10 5DD, UK;2. School of Chemistry, Newcastle University, Newcastle upon Tyne NE1 7RU, UK |
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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 pKaH. 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. |
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Keywords: | Cyanohydrin Ethyl cyanoformate Base Catalysis Kinetics |
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