NEW CYCLOADDITION REACTIONS OF SOME ETHENYL AND ETHINYL[2.2]PARACYCLOPHANES WITH SOME DIENOPHILES

4-Ethenyl[2.2]paracyclophane (1), 4,12-, (13), 4,15-, (16) and 4,16-diethenyl[2.2]paracyclophane (18) as well as, 4-ethinyl-[2.2]paracyclopane (20) undergo[2+2]cycloaddition reactions with tetra-cyanoethylene (TCNE). These reactions involve the formation of a charge-transfer complex as an initial step. With 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ), bromanil (BRL) as well as 4-phenyl-1,2,4-triazoline-3,5-dione and 4-ethenyl[2.2]paracyclophane (1) as the diene, [2+4]cycloadditions took place. The reaction between 4,12-, (13), 4,15-, (16) and 4,16-, diethenyl[2.2]paracyclophane (18) and TCNE are influenced by the transannular electronic interactions.