Cyclophanes. IV. Synthetic approaches to cyclophane dienes. The preparation of [2,2](2,7)Naphthalenophane-1,11-diene

Abstract

The synthesis of [2,2](2,7)naphthalenophane-1,ll-diene (2a) from 2,13-dithia[3,3](2,7)naphthalenophane (4) by means of a Stevens rearrangement ring contraction and a Hofmann elimination procedure is described. The diene was found to undergo an efficient oxidative photochemical cyclization to coronene. Several other reactions of the naphthalenophane ring system are described, and the stereochemistry of the macrocycle is discussed.