The structures of the 1:1 and 1:2 addition products of dicyanoacetylen
e (2) to [2.2]paracyclophane (1) have been determined by X-ray structu
ral analysis as 3 and 5, respectively. In contrast to literature repor
ts, the latter possesses the ''crossed'' double barrelene configuratio
n. On irradiation 3 isomerizes to the semibullvalenophane 4 as was als
o shown by X-ray structural analysis.