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Photochromism of 3H-2,1,4-benzoxadiazine 4-oxides with heterocyclic substituents on the benzene ring


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Abstract

2H-Benzimidazole 1,3-dioxides undergo thermal isomerization to 3H-2,1,4-benzoxadiazine 4-oxides which are converted to 2H-benzimidazole 1-oxides on further heating. Irradiation of 3H-2,1,4-benzoxadiazine 4-oxides with sunlight induces their transformation to 2H-benzimidazole 1,3-dioxides. 3H-2,1,4-Benzoxadiazine 4-oxides containing nucleophilic heterocyclic substituents are considerably more stable to sunlight, and they can be used as photochromic compounds.

About the authors

E. A. Chugunova

Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center

Author for correspondence.
Email: elena-chugunova@list.ru
Russian Federation, ul. Arbuzova 8, Kazan Tatarstan, 420088

N. I. Akylbekov

Kazan National Research Technological University

Email: elena-chugunova@list.ru
Russian Federation, ul. Karla Marksa 68, Kazan Tatarstan, 420015

V. A. Samsonov

Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch

Email: elena-chugunova@list.ru
Russian Federation, pr. Akademika Lavrent’eva 9, Novosibirsk, 630090

S. A. Sitnov

Kazan Federal University

Email: elena-chugunova@list.ru
Russian Federation, ul. Kremlevskaya 18, Kazan Tatarstan, 420008

A. R. Burilov

Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center

Email: elena-chugunova@list.ru
Russian Federation, ul. Arbuzova 8, Kazan Tatarstan, 420088

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