Cyclophanes. VIII. An attempted preparation of [7]circulene from [2,2](3,6)Phenanthro(2,7)naphthalenophane-1,11-diene

Abstract

The synthesis of [2,2](3,6)phenanthro(2,7)naphthalenophane-1,11-diene (13) from 2,13-dithia[3,3]-(3,6)phenanthro(2,7)naphthalenophane (6) is described. Attempts to oxidatively cyclize the diene (13)to [7]circulene (3) failed, and these observations have been rationalized in terms of the probable syn stereochemistry of the diene (13). Several other reactions of the phenanthronaphthalenophane ring system are described.