23225-88-9

Upstream product

• 13146-23-1 copper(I) phenylacetylenide 
• 670-54-2 ethenetetracarbonitrile 
• 536-74-3 phenylacetylene 
• 833447-41-9 tert-butyl tricyanoethylenecarboxylate 

Downstream Products

• 135513-89-2 3,4-di(1,3-dithiol-2-ylidene)-4-phenylbut-1-ene-1,1,2-tricarbonitrile 

Relevant academic research and scientific papers

Dynamic Diels-Alder reactions of 9,10-dimethylanthracene: Reversible adduct formation, dynamic exchange processes and thermal fluorescence modulation

Studies of the Diels-Alder reactions between 9,10-dimethylanthracene and cyano-functionahzcd dienophiles led to the identification and characterization of new dynamic systems under ambient conditions. Among these dienophiles were tricyanoethynylethylene d

Synthesis and Electrochemical Properties of 4-Phenyl-1-buten-3-yne-1,1,2-tricarbonitriles and Tricyanoacrylates

The reaction of phenylacetylenes 4a-h 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 synthesised 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 acetonitrile and react irreversibly with 6 to give oligomeric anions 6.-n.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 6h2.-.By contrast, the tricyanoacrylates 8 can be reversibly reduced to their respective radical anions and dianions. - Keywords: Cyano compounds, conjugated / Phenylacetylenes / Radical anions / Electrochemistry