Synthesis and structures of [2n](2,7)naphthalenophanes (n = 2–4)

Abstract

Reductive coupling of 2,7-bis(bromomethyl)naphthalene using phenyllithium gave anti-[22](2,7)naphthalenophane, [23](2,7)naphthalenophane, and [24](2,7)naphthalenophane, the distribution of which was dependent on the reaction conditions. The structure of the first compound was established by X-ray crystallographic analysis. On the basis of the similarity between the NMR and UV spectra of [23](2,7)naphthalenophane with those reported for syn-[22](2,7)naphthalenophane, we conclude that the compound originally assigned to be syn-4 was in fact 6.