Kinetics and thermochemistry of [2π + 2σ + 2σ]-cycloaddition of quadricyclane to tetracyanoethylene


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Abstract

Kinetic data for the unusual [2π + 2σ + 2σ]-cycloaddition of quadricyclane to tetracyanoethylene in toluene have been obtained for the first time. The same reaction in 1,4-dioxane appears to be the most exothermic among known cycloaddition reactions. The entropy of activation and reaction volume differ only slightly from the corresponding parameters of conventional Diels–Alder reactions.

About the authors

V. D. Kiselev

Butlerov Institute of Chemistry

Author for correspondence.
Email: vkiselev.ksu@gmail.com
Russian Federation, ul. Kremlevskaya 18, Kazan, Tatarstan, 420008

D. A. Kornilov

Butlerov Institute of Chemistry

Email: vkiselev.ksu@gmail.com
Russian Federation, ul. Kremlevskaya 18, Kazan, Tatarstan, 420008

O. V. Anikin

Butlerov Institute of Chemistry

Email: vkiselev.ksu@gmail.com
Russian Federation, ul. Kremlevskaya 18, Kazan, Tatarstan, 420008

L. I. Latypova

Butlerov Institute of Chemistry

Email: vkiselev.ksu@gmail.com
Russian Federation, ul. Kremlevskaya 18, Kazan, Tatarstan, 420008

M. V. Bermeshev

Topchiev Institute of Petrochemical Synthesis

Email: vkiselev.ksu@gmail.com
Russian Federation, Leninskii pr. 29, Moscow, 119991

P. P. Chapala

Topchiev Institute of Petrochemical Synthesis

Email: vkiselev.ksu@gmail.com
Russian Federation, Leninskii pr. 29, Moscow, 119991

A. I. Konovalov

Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center

Email: vkiselev.ksu@gmail.com
Russian Federation, ul. Arbuzova 8, Tatarstan, Kazan, 420088

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