Novel [2.2]paracyclophane derivatives via charge-transfer complexation

The transannular electronic interactions in [2.2]paracyclophanes affect the selectivity of the tricyanovinylation reaction with tetracyanoethylene (TCNE). In addition to the normal N-tricyanovinyl product, 4-amino[2,2]paracyclophane reacts with TCNE to give oxaziridine derivatives. In the case of reaction with 4-N-methylamino[2.2]paracyclophane, the unusual N-tricyanovinylated product as well as 4-(N-carbonitrile-N-methyl)annino[2.2]paracyclophane was isolated. The reaction of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) with 4-amino[2.2]paracyclophane results in formation of 2-cyano-3-(4-[2.2]paracyclophanyl)amino-5,6-dichloro-1,4-benzoquinone.