1993 年 51 巻 7 号 p. 652-663
Various [2.n] cyclophanes, [2.n] naphthalenophanes, and [2.n] phenanthrenophanes having cyclobutane rings were prepared, in most cases stereoselectively, by intramolecular [2+2] photocycloaddition of α, ω-bis(vinylaryl)alkanes. This facile reaction is reviewed. The stereoselectivity is recognized in the syntheses of syn-naphthalenophanes and syn-phenanthrenophanes. The reaction mechanism is discussed with flash-photolysis data and solvent and additive effects. Combined with a cationic cyclocodimerization and Birch reduction, this reaction presents a systematic synthesis of [2.n]-, [3.n]-, and [4.n]-cyclophanes form only one common starting materials, α, ω-bis(vinylaryl)alkanes. Crown compounds were also synthesized by this reaction in excellent yields. They showed an interesting Li+-ion selectivity in solvent extraction and transport experiments.