Issue 0, 1979

Thermal and photochemical reactions of charge-transfer complexes of tetracyanoethylene–toluene systems

Abstract

Irradiation of the charge-transfer (CT) absorption bands of tetra cyanoethylene (TCNE)–toluene systems gave 3-phenylpropane-1,1,2,2-tetracarbonitrile. TCNE-xylene systems gave a similar addition product on both irradiation of the CT bands and heating under reflux. These reactions proceed through electron-transfer followed by proton-transfer. TCNE reacts with methanol thermally in the presence of NN-dimethyl-p-toluidine to yield dicyanoketen dimethylacetal which alkylates the toluidine to give eventually NNN-trimethyl-p-toluidinium 2,2-dicyano-1-methoxyethenolate. m-Toluidine reacted similarly and the corresponding toluidinium salt was obtained in addition to a tricyanovinylated product. Irradiation of NN-dimethyl-p-toluidine with TCNE in methanol gave a diphenyl derivative together with N-cyanomethyl-N-methyl-p-toluidine through radical reactions of the thermal reaction products, NNN-trimethyl-p-toluidinium salts.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1979, 2219-2223

Thermal and photochemical reactions of charge-transfer complexes of tetracyanoethylene–toluene systems

M. Ohashi, S. Suwa, Y. Osawa and K. Tsujimoto, J. Chem. Soc., Perkin Trans. 1, 1979, 2219 DOI: 10.1039/P19790002219

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements