The pyridine-catalysed reaction of methanol with phenyl isocyanate in tetrachloromethane
- 1 January 1981
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 4,p. 664-669
- https://doi.org/10.1039/p29810000664
Abstract
The title reaction is first order in catalyst and each reactant. Several 3- and 4-substituted pyridine catalysts generate a Brönsted plot with slope β of 0.49. This, the steric effect of 2,4,6-trimethylpyridine, the deuterium isotope effect, and the solvent effect are consistent with the general base mechanism of catalysis. The nucleophilic mechanism is considered relatively unlikely. 2-Pyridylmethanol reacts with phenyl isocyanate faster than does 4-pyridylmethanol, indicating intramolecular general base catalysis in the former case.Keywords
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