NOVEL [2.2]PARACYCLOPHANE DERIVATIVES VIA CHARGE-TRANSFER COMPLEXATION

The transannular electronic interactions in [2.2]paracyclophanes affec t the selectivity of the tricyanovinylation reaction with tetracyanoet hylene (TCNE). In addition to the normal N-tricyanovinyl product, 4-am ino[2.2]paracyclophane reacts with TCNE to give oxaziridine derivative s. In the case of reaction with 4-N-methylamino[2.2]paracyclophane, th e unusual N-tricyanovinylated product as well as -(N-carbonitrile-N-me thyl)amino[2.2]paracyclophane was isolated. The reaction of 2,3-dichlo ro-5,6-dicyano-1,4-benzoquinone (DDQ) with 4-amino[2.2]paracyclophane results in formation of racyclophanyl)amino-5,6-dichloro-1,4-benzoquin one.