期刊
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
卷 45, 期 1, 页码 68-73出版社
MAIK NAUKA/INTERPERIODICA/SPRINGER
DOI: 10.1134/S1070428009010096
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Addition of linear methanol associates at the C=O group of phenyl isocyanate involves a concerted cyclic asymmetric late transition state. The reaction is accompanied by formation of pre- and post-reaction complexes. Isomerization of intermediate methyl hydrogen phenylimidocarbonate into methyl phenylcarbamate is characterized by a considerable energy barrier. The reactivity of methanol molecules increases in parallel with the degree of their association, which is related to increase in their electron-donor power. Comparison of the calculated parameters for the addition of methanol associates at the C=N and C=O bonds of phenyl isocyanate clearly indicates that the first path is preferred.
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