有機合成化学協会誌
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
タンデムクライゼン転位 : 新規機能性フエノール誘導体の構築
平谷 和久名川 吉信徳久 英雄小山 恵美子
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2003 年 61 巻 2 号 p. 111-122

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The reaction of 3-chloro-2-chloromethyl-l-propene with 2 equimolar phenolic compounds gave isobutenyl bis (aryl) ether compounds. The thermal or Lewis acid-assisted Claisen rearrangement of the ether compounds results in generating phenolic compounds having plural hydroxyl groups at one step reaction. We named this reaction as “tandem Claisen rearrangement, ” where the Claisen rearrangement successively occurs two times at each isobutenyl ether moiety. This reaction can be applied not only to acyclic, but also to macrocyclic compounds having isobutenyl ether moiety. Tetradentate ligands with two quinolinol moieties, tripodal hexadentate ligands with either three quinolinol or catechol moieties, etc. have been synthesized as acyclic rearranged products. As macrocyclic rearranged products, various kinds of novel crownophane and cyclophane derivatives having plural hydroxyl groups have been synthesized. These compounds prepared via tandem Claisen rearrangement have been found to be able to work as ionophore, fluorophore, host molecules for neutral organic molecules, chiral ones, ligands for transition metal ions and so on.

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