Investigation of the Mechanism of the Alkylation Reaction of 2-Methylimidazole 1,1,3,3-Tetraiodpropane-2-on by the MALDI Method

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Abstract

The mechanism of the alkylation reaction of 2-methylimidazole with 1,1,3,3-tetraiodopropan-2-one in the absence and presence an acceptor (CaCO3) of hydrogen iodide using laser desorption/ionization was studied for the first time. The composition of the reaction mixtures and possible routes for the formation of functionalized 2-methylimidazole derivatives were determined. N1 and N1,3-alkylation of 2-methylimidazole with reduced (1-iodopropan-2-one, 1,3-diiodopropan-2-one) or dehydroiodinated (2,3-diiodo-2-cyclopropen-1) forms 1,1, 3,3-tetraiodoproapan-2-one is a crucial step in the synthesis. The thermodynamic and kinetic characteristics of the reduction and dehydroiodination of 1,1,3,3-tetraiodoacetone were evaluated by quantum-chemical calculations using the [B3LYP/6-311+G(d,p)+dgdzvp) basis set.

About the authors

L. V. Klyba

A.E. Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences

Author for correspondence.
Email: klyba@irioch.irk.ru
ORCID iD: 0000-0002-5521-3201
Russian Federation, Favorsky St., 1, Irkutsk, 664033

E. R. Sanzheeva

A.E. Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences

Email: klyba@irioch.irk.ru
ORCID iD: 0000-0002-9776-2794
Russian Federation, Favorsky St., 1, Irkutsk, 664033

I. A. Dorofeev

A.E. Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences

Email: klyba@irioch.irk.ru
ORCID iD: 0000-0003-4646-6554
Russian Federation, Favorsky St., 1, Irkutsk, 664033

V. A. Shagun

A.E. Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences

Email: klyba@irioch.irk.ru
ORCID iD: 0000-0002-2189-7043
Russian Federation, Favorsky St., 1, Irkutsk, 664033

G. A. Fedorova

Limnological Institute, Siberian Branch of the Russian Academy of Sciences

Email: klyba@irioch.irk.ru
ORCID iD: 0000-0002-1697-8631
Russian Federation, Ulan-Batorskaya St, 3, Irkutsk, 664033

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