
%0 Journal Article
%A Jessup, PJ 
%A Reiss, JA 
%T Cyclophanes. VI. The synthesis of [2,2](3,3')biphenylparacyclophanedienes
%J Australian Journal of Chemistry
%D 1976/06/01
%V 29
%N 6
%P 1267-1275
%K 
%R https://doi.org/10.1071/CH9761267
%U https://www.publish.csiro.au/paper/CH9761267 
%X The preparations of [2,2](3,3')biphenylparacyclophane-1,9-dine (19) and a dimethyl derivative (20) synthesized by a ring-contraction procedure of the corresponding dithiacyclophanes (11) and (12) are reported. Both dienes (19) and (20) photocyclized under oxidative conditions to the benzo[ghi]- perylenes (21) and (22). Difficulties associated with the Stevens rearrangement in cyclophanes containing a para-disubstituted benzene moiety have been rationalized in terms of a competing ring- opening reaction. Several other reactions of the biphenylparacylophane ring system are reported, and the stereochemistry of the macrocycle is discussed. 
