Isolation of macrocyclic metacyclophanes from the attempted synthesis of [7.0]metacyclophanes of the myricanone series by Thorpe-Ziegler intramolecular cyclization of diaryls substituted by omega-cyanoalkyl chains

The syntheses of the diaryls 14 and 21, substituted by two omega-cyanoalkyl chains (one on each ring), are described. Treatment of the unsymmetrical d iaryl 14 with NaN(Me)Ph in a Thorpe-Ziegler reaction failed to give any def inite product. Under the same conditions the symmetrical diaryl 21 led to a n isomeric mixture of dimeric enaminonitriles 24. Mild acidic hydrolysis of the latter yielded the isomeric beta-ketonitriles 25, whereas more drastic hydrolytic conditions led to the macrocyclic diketone 26.