Variable Activity of Reagents with C=C and N=N Bonds in Cycloaddition Reactions |
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Authors: | O V Anikin D A Kornilov T V Nikitina V D Kiselev |
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Institution: | 1.Butlerov Institute of Chemistry,Kazan (Volga Region) Federal University,Kazan, Tatarstan,Russia |
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Abstract: | Data on rates and enthalpies of the reactions of quadricyclane (4) and diadamantylidene (5) with N-phenylmaleimide (1), 4-phenyl-1,2,4-triazoline-3,5-dione (2), and tetracyanoethylene (3) are obtained for the first time. Reagent 2 with the N=N reaction center is found to be six orders of magnitude more active than its structural analog 1. A strong π-acceptor 3 is 370 times more active than reagent 2 in the reaction with a strong π-donor substrate 4 but is less active than reagent 2 in many 4π + 2π], 2π + 2π + 2π], and 2π + 2π] cycloaddition reactions, and, especially, in ene reactions. The possible causes of the strong difference and variable activity of compounds 1–3 with C=C and N=N bonds are discussed. |
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