ORTHOCYCLOPHANES .4. FUNCTIONALIZATION OF [1(N)]ORTHOCYCLOPHANES ON THE AROMATIC RINGS

Functionalization of the [1(n)]orthocyclophanes ([1(n)]OCPs) has been accomplished by introducing groups on the aromatic rings of the cycles. Dilithiation of dibromoaromatic 10 followed by condensation with various aromatic dialdehydes, such as 14, 20, and 30, gave rise to [1(n)]OCP cycles bearing methoxy groups on the aromatic rings. Several polymethoxy[1(n)]OCPs have been prepared that are reasonably soluble inorganic solvents, in contrast to their parent hydrocarbons. Since methoxy functions can be converted to phenolic hydroxy groups and then to other functionalities, the methoxy derivatives may have broad applications to the modification of [1(n)]OCPs for the preparation of a variety of supramolecules.