Folding-promoted TBACl-mediated chemo- and regioselective demethylations of methoxybenzene-based macrocyclic pentamers

Org Lett. 2011 Dec 2;13(23):6212-5. doi: 10.1021/ol202658p. Epub 2011 Nov 2.

Abstract

Tetrabutylammonium chloride (TBACl) salt alone has not been shown previously to be capable of removing methoxy groups. It is demonstrated here that the use of TBACl achieves efficient folding-promoted chemo- and regioselective demethylations, eliminating up to two out of five methyl groups situated in similar macrocyclic chemical microenvironments.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Methylation
  • Models, Molecular*
  • Molecular Structure
  • Quaternary Ammonium Compounds / chemistry*
  • Stereoisomerism

Substances

  • Quaternary Ammonium Compounds
  • tetrabutylammonium