Synthesis and electrochemical properties of 4-phenyl-1-buten-3-yne-1,1,2-tricarbonitriles and tricyanoacrylates
| Autor: | Bernd Körner, Jianjun Yang, Lothar Dulog, Jürgen Heinze |
|---|---|
| Rok vydání: | 1995 |
| Předmět: |
chemistry.chemical_classification
Organic Chemistry Analytical chemistry Halide chemistry.chemical_element General Chemistry Tetracyanoethylene Electron acceptor Electrochemistry Medicinal chemistry Copper Catalysis chemistry.chemical_compound chemistry Pyridine Physical and Theoretical Chemistry Acetonitrile |
| Zdroj: | Liebigs Annalen. 1995:1663-1671 |
| ISSN: | 1099-0690 0947-3440 |
| DOI: | 10.1002/jlac.1995199509231 |
| Popis: | The reaction of phenylacetylenes 4a–h with copper(I) acetate (5) and TCNE (tetracyanoethylene) in THF/acetonitrile gave 4-phenyl-1-buten-3-yne-1,1,2-tricarbonitriles 6a–h. 4i did not react to give 6i. The phenylacetylenes 4b–i were prepared by a two-step synthesis starting from the corresponding phenyl halides 1b–i. The tricyanoacrylates 8 were synthesized from the corresponding cyanoacetates 7, TCNE and catalytic amounts of pyridine in THF. – Cyclovoltammetric investigations showed that the butenynes 6 and the tricyanoacrylates 8 are strong electron acceptors which can be easily reduced. The radical anions 6˙− are unstable in aceto-nitrile and react irreversibly with 6 to give oligomeric anions 6. Only 4-(2,4,6-trimethoxyphenyl)-1-buten-3-yne-1,1,2-tricarbonitrile (6h) is reduced to a radical anion 6h˙− which associates with 6h in a reversible follow-up process to form a dimeric anion 6h. By contrast, the tricyanoacrylates 8 can be reversibly reduced to their respective radical anions and dianions. |
| Databáze: | OpenAIRE |
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