Abstract
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.
Cited by
18 articles.
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