Synthesis and conformational studies of calixarene analogue chiral [3.3.1]metacyclophanes

Md Monarul Islam, Tomiyasu Hirotsugu, Pierre Thuery, Taisuke Matsumoto, Junji Tanaka, Mark R.J. Elsegood, Carl Redshaw, Takehiko Yamato

研究成果: ジャーナルへの寄稿学術誌査読

16 被引用数 (Scopus)

抄録

Trihydroxy[3.3.1]metacyclophane, which can be regarded as an unsymmetrical or incomplete "homocalix[3]arene", has been prepared from trimethoxy[3.3.1]metacyclophane by demethylation with trimethylsilyl iodide in MeCN. Di-O-methylation at the lower rim of trihydroxy[3.3.1]metacyclophane in the presence of K2CO3 in acetone afforded a novel, inherently chiral calixarene-analogue, namely a macrocyclic [3.3.1]metacyclophane, possessing C1 symmetry. The inherent chirality of the two conformers was characterized by 1H NMR spectroscopy by addition of an excess of Pirkle's chiral shift reagent [(S)-(+)-1-(9-anthryl)-2,2,2-trifluoroethanol], which caused a splitting of the OMe group and AB patterns corresponding to the methylene protons.

本文言語英語
ページ(範囲)47-54
ページ数8
ジャーナルJournal of Molecular Structure
1098
DOI
出版ステータス出版済み - 6月 12 2015

!!!All Science Journal Classification (ASJC) codes

  • 分析化学
  • 分光学
  • 有機化学
  • 無機化学

フィンガープリント

「Synthesis and conformational studies of calixarene analogue chiral [3.3.1]metacyclophanes」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル