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ЖУРНАЛЫ // Mendeleev Communications // Архив

Mendeleev Commun., 2022, том 32, выпуск 2, страницы 167–169 (Mi mendc601)

Эта публикация цитируется в 6 статьях

Communications

Radical oxyamination of vinyl azides with N-hydroxyphthalimide under the action of [bis(trifluoroacetoxy)iodo]benzene

S. A. Pavelieva, O. O. Segidaa, U. V. Fedorovab, O. M. Mulinaa, A. O. Terent'eva

a N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
b D.Mendeleev University of Chemical Technology of Russia, Moscow, Russian Federation


Аннотация: O,O′-Bis(phthalimido)-modified 2-(hydroxyimino)ethanols containing N–O–N fragment were synthesized in high yields via the reaction of vinyl azides with N-hydroxyphthalimide under the action of hypervalent iodine-based oxidant. The reaction proceeds under mild conditions and is compatible with a wide range of vinyl azides. Presumably, the process starts with the oxidative formation of phthalimide-N-oxyl radical, followed by its addition to vinyl azide with the subsequent trapping of the generated iminyl radical with the second phthalimide-N-oxyl radical.

Ключевые слова: free radicals, imides, N-oxyl radicals, N-hydroxyphthalimide, vinyl azides, hypervalent iodine.

Язык публикации: английский

DOI: 10.1016/j.mencom.2022.03.004



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