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Keywords = butadiene-1,1,2,2-tetracarbonitriles

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38 pages, 40485 KiB  
Review
Reactions of Tetracyanoethylene with Aliphatic and Aromatic Amines and Hydrazines and Chemical Transformations of Tetracyanoethylene Derivatives
by Elizaveta Ivanova, Margarita Osipova, Yhtyyar Kadyrov, Sergey Karpov, Svetlana Markova, Ekaterina Zazhivihina, Lubov Umanova, Tatyana Vasilieva, Yurii Mitrasov, Yulia Smolkina and Oleg Nasakin
Molecules 2024, 29(19), 4727; https://doi.org/10.3390/molecules29194727 - 6 Oct 2024
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Abstract
The significant synthetic potential and reactivity of tetracyanoethylene (TCNE) have captured the interest of numerous chemical communities. One of the most promising, readily achievable, yet least explored pathways for the reactivity of TCNE involves its interaction with arylamines. Typically, the reaction proceeds via [...] Read more.
The significant synthetic potential and reactivity of tetracyanoethylene (TCNE) have captured the interest of numerous chemical communities. One of the most promising, readily achievable, yet least explored pathways for the reactivity of TCNE involves its interaction with arylamines. Typically, the reaction proceeds via tricyanovinylation (TCV); however, deviations from the standard chemical process have been observed in some instances. These include the formation of heterocyclic structures through tricyanovinyl intermediates, aliphatic dicarbonitriles through the cleavage of the C–C bond of a tetracyanoethyl substituent, complexation, and various pericyclic reactions. Therefore, the objective of this study is to review the diverse modes of interaction of TCNE with aromatic nitrogen-containing compounds and to focus the attention of the chemical community on the synthetic capabilities of this reagent, as well as the various biological and optical activities of the structures synthesized based on TCNE. Full article
(This article belongs to the Section Organic Chemistry)
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