The Benzene Ring as a Dipolarophile: Reactions of Monosubstituted Benzenes with Tetracyanoethylene Oxide

Article abstract of DOI:10.1007/BF01045302

The reaction of tetracyanoethylene oxide on one hand and toluene, chlorobenzene, fluorobenzene, anisole, and nitrobenzene, on the other, has been studied.Toluene and the halogenobenzenes yield mixtures of monoadducts, anisole yield p-methoxyphenylmalononitrile and its dimer and nitrobenzene does not react.These results are discussed with the help of a qualitative orbital model. 1H-NMR analysis of some monoadducts has been carried out.Keywords: Benzene derivatives; Tetracyanoethylene oxide; 1,3-Dipolar cycloaddition.