有機合成化学協会誌
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
ビニル芳香族化合物の光環化付加反応によるシクロファン類の合成とその性質
竹内 基晴猪熊 精一西村 淳
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1993 年 51 巻 7 号 p. 652-663

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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.

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