Cyanocarbon Chemistry. XIX.^1,2 Tetracyanocyclobutanes from Tetracyanoethylene and Electron-rich Alkenes

The structure of poly(N‐vinylcarbazole) obtained with cationic initiators and electron acceptors as catalysts

“…Williams et al, 23) reported that TCNE reacts with electron-donating alkenes, such as p-methoxystyrene, VCz, and methyl vinyl ether, to produce cyclobutane compounds. They assigned the structure of the precipitate produced in the reaction of VCz with TCNE in THF as 1-(2,2,3,3-tetracyanocyclobutyl) Tamaru et al 12) employed this precipitate to initiate the polymerization of VCz.…”

1,4‐Dioxo‐1,4‐dihydronaphthalene‐2,3‐dicarbonitrile and 1,1,2,2‐Tetracyanoethene in Heterocyclization

“…Cyano groups in 1,1,2,2‐tetracyanoethene (TCNE, 2 ) have low‐energy π* orbitals, and the presence of four such groups, with their π systems linked (conjugated) to the central C=C double bond, gives rise to an excellent acceptor . In general, TCNE and its derivatives containing the dicyanovinylidene moiety are electron‐deficient substances, and it is well known that their monoelectronic reduction usually results in the formation of fairly long‐lived radical anions ; this also applies to other species containing cyano groups bound to a double bond .…”

Solvent, Temperature, and Pressure Effects on the Reaction Between Tetracyanoethylene and Styrene

“…As mentioned above, p-methoxystyrene(PMS) cycloadds thermally to TCNE rapidly in a polar solvent like CH2Cl2 and very very slowly in a non-polar solvent like CCl4. 2) In the chilled solution of PMS and TCNE in CCl4, the new species formation is too fast to be followed from the beginning by the usual technique, but if the spectra are measured within a minute of mixing a slight increase of absorption in the corresponding region is really observable with an isosbestic point near 365nm as shown in Fig. 3.…”