キハラ ノブヒロ   Kihara Nobuhiro
  木原 伸浩
   所属   神奈川大学  理学部 化学科
   職種   教授
言語種別 英語
発行・発表の年月 2006/07
形態種別 学術雑誌
査読 査読あり
標題 Sequential O- and N-Acylation Protocol for High-Yield Preparation and Modification of Rotaxanes: Synthesis, Functionalization, Structure, and Intercomponent Interaction of Rotaxanes
執筆形態 共著
掲載誌名 J. Org. Chem.
巻・号・頁 71(14),pp.5093-5104
著者・共著者 Yuya Tachibana, Hiroaki Kawasaki, Nobuhiro Kihara, Toshikazu Takata
概要 A pseudorotaxane consisting of a 24-membered crown ether and secondary ammonium salt with the hydroxy group at the terminus was quant. acylated by bulky acid anhydride in the presence of tributylphosphane as catalyst to afford the corresponding rotaxane in high yield. The ammonium group in the resulting rotaxane was quant. acylated with excess electrophile in the presence of excess trialkylamine. 1H NMR spectra and X-ray crystallog. analyses of the rotaxanes showed that the crown ether component was captured on the ammonium group in ammonium-type rotaxane by strong hydrogen-bonding intercomponent interaction. The conformation around the ammonium group was fixed by the hydrogen-bonding interaction. Meanwhile, the conformation of the amide-type rotaxane was detd. by the weak CH/π interaction. The N-acylation of ammonium-type rotaxane is useful for the prepn. of both functionalized rotaxanes and weak intercomponent interaction-based rotaxanes.
DOI 10.1021/jo0601563
ISSN 0022-3263