Three groups good, four groups bad? Atropisomerism in ortho-substituted diaryl ethers

Mark S. Betson*, Jonathan Clayden, Christopher P. Worrall, Simon Peace

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

43 Citations (Scopus)

Abstract

(Chemical Equation Presented) Bring on the substitute: Even outside of macrocyclic structures, such as vancomycin, appropriate substitution can give rise to atropisomerism in diaryl ethers. Stereochemical stability about the Ar-OAr axis at room temperature or above is possible when neither of the rings is symmetrically substituted and when at least one ring carries an ortho tert-butyl group or equivalent.

Original languageEnglish
Pages (from-to)5803-5807
Number of pages5
JournalAngewandte Chemie - International Edition
Volume45
Issue number35
Early online date28 Jul 2006
DOIs
Publication statusPublished - 4 Sep 2006

Keywords

  • Atropisomerism
  • Diaryl ethers
  • NMR spectroscopy
  • Rotational barriers
  • Stereochemistry

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