Univerzita Pardubice Fakulta chemicko- technologická

Univerzita Pardubice

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Publikace detail

Influence of substitution on 1,3-dipolar cycloadition of arylsydnone and arylacetylene

Autoři: Hladíková Veronika | Hanusek Jiří

Rok: 2017

Druh publikace: ostatní - přednáška nebo poster

Strana od-do: nestránkováno

Tituly:

Jazyk	Název	Abstrakt	Klíčová slova
eng	Influence of substitution on 1,3-dipolar cycloadition of arylsydnone and arylacetylene	1,3-Dipolar cycloaddition of sydnones with alkynes was published in 1962 by Huisgen [1] and since then this reaction has been extensively studied. This reaction provides a mixture of pyrazoles under harsh conditions [2] while under milder conditions only one regioisomer. Recently Kolodych et al. reported copper-catalyzed sydnone-alkyne regioselective cycloaddition under milder conditions providing higher yield (Scheme 1).[3] The kinetic study on their formation hasn´t appeared until now so we performed HPLC kinetic study of Cu-mediated cycloaddition of N arylsydnones with terminal arylacetylenes (CuSAC). The reaction rate was measured under various conditions. For the reaction of N-arylsydnone with arylacetylene it was found that kinetic rate is dependent on starting concentration of N arylsydnone but independent on the starting concentration of arylacetylene and also depends on the amount of copper and amount and type of the ligand. Influence of substitution depends on polar effect of the substituent. Electron donor substituents accelerate kinetic rate in contrast to the electron acceptors that slow it down (relative to the standard H).