Catalytic Metathesis of N-Methylformamide with Dimethyl Carbonate by Alcohol Associates

The mechanism of N -methylformamide metathesis with dimethyl carbonate, which leads to the formation of N , O -dimethyl carbamate, is studied using the quantum-chemical B3LYP/6-311++G( df,p ) approach. The reaction consists of three stages: the conversion of formamide to iminol; the adding of dimeth...

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Bibliographic Details
Published in:Russian Journal of Physical Chemistry A 2019-12, Vol.93 (12), p.2365-2372
Main Authors: Samuilov, A. Ya, Alekbaev, D. R., Samuilov, Ya. D.
Format: Article
Language:English
Subjects:
Chemical Kinetics and Catalysis
Chemistry
Chemistry and Materials Science
Dimers
Metathesis
Methyl formate
Organic chemistry
Physical Chemistry
Quantum chemistry
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Summary:The mechanism of N -methylformamide metathesis with dimethyl carbonate, which leads to the formation of N , O -dimethyl carbamate, is studied using the quantum-chemical B3LYP/6-311++G( df,p ) approach. The reaction consists of three stages: the conversion of formamide to iminol; the adding of dimethyl carbonate at the azomethine bond of iminol; and decomposition of the resulting product into carbamate and methyl formate. The second stage limits the rate of interaction. All stages proceed through concerted cyclic transition state, and all of them are catalyzed efficiently by a monomer and a dimer of methanol.
ISSN:0036-0244
1531-863X
DOI:10.1134/S0036024419120240