Реферат: Azines are easily available products of condensation between carbonyl compounds and hydrazine and at first glance look like perfect radical acceptors, azadienes. However, their free-radical chemistry is almost not developed due to relative inertness associated with the unusual behavior of the C═N─N═C fragment as a “conjugation stopper”. In the present work, the radical functionalization of azines by the addition of imide-N-oxyl radicals affording of bis-(imide-N-oxy) azocompounds is reported. The transformation proceeds through the generation of imide-N-oxyl radicals from N-hydroxyimides under room temperature and metal-free conditions. It is noteworthy that the addition of two equivalents of N-oxyl radicals occurs selectively, without the formation of products of hydrogen atom abstraction or other transformations of intermediate N, C-centered radicals (oxidation, dimerization, fragmentation, etc.). A broad range of ketazines and aldazines derived from aromatic and aliphatic carbonyl compounds are efficiently converted, demonstrating good functional-group tolerance. Notably, thermal decomposition of the NHPI-derived azo-ethers was found to generate phthalimide radicals. This work expands the radical chemistry of azines and provides a rare one-step approach to azo-ethers from readily accessible azines and N-hydroxyimides.

Библиографическая ссылка: Shevchenko M.I. , Budnikov A.S. , Monin F.K. , Krylov I.B. , Sokova L.L. , Terent’ev A.O.
Imide‐ N ‐Oxyl Radicals in the Synthesis of Functionalized Azocompounds From Azines via Challenging Radical Addition to C═N─N═C Fragment
European Journal of Organic Chemistry. 2026. e70672 . DOI: 10.1002/ejoc.70672 OpenAlex

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Поступила в редакцию:	20 мар. 2026 г.
Опубликована в печати:	15 июл. 2026 г.

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W7168399831

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