Syntheses and NMR Spectroscopic Studies of Bridged and Capped Calix[6]arenes: High-Yield Syntheses of Unimolecular Caged Compounds from Calix[6]arene

Hideyuki Otsuka, Koji Araki, Hitoshi Matsumoto, Takaaki Harada, Seiji Shinkai

研究成果: Contribution to journalArticle査読

58 被引用数 (Scopus)

抄録

Calix[6]arenes were bridged with a xylenyl unit or capped with a mesitylenyl unit, and their conformational properties were examined by spectroscopic methods. As previously reported by Gutsche et al., the calix[6]arene bridged on 1, 4-phenyl units could enjoy slow ring inversion. The calix[6]arene bridged on 1, 2-phenyl units also showed the ring inversion behavior, whereas in the calix[6]arene bridged on 1, 3-phenyl units, ring inversion was virtually suppressed because of destabilization of the transition state. The capping of 1, 3,5-tri-O-alkylated calix[6]arenes with 1, 3,5-tris(bromomethyl)benzene gave the products in high yields (80–91%). This advantage was accounted for by the C3 symmetrical complementarity of these two reactants. In these capped products, ring inversion was inhibited under the present measurement conditions, and the presence of a unimolecularly closed inner cavity was suggested on the basis of 1H NMR spectroscopy and MM3 calculations.

本文言語英語
ページ(範囲)4862-4867
ページ数6
ジャーナルJournal of Organic Chemistry
60
15
DOI
出版ステータス出版済み - 7 1 1995

All Science Journal Classification (ASJC) codes

  • 有機化学

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