Investigations into the role of ion pairing in reactions of heteroatom-substituted cyclic oxocarbenium ions

Org Lett. 2005 Mar 17;7(6):1157-60. doi: 10.1021/ol0500620.

Abstract

[reaction: see text] The O-to-C rearrangement of vinyl acetals is used to demonstrate that tight ion pairing is not involved in the stereoselective nucleophilic addition reactions of alkoxy-substituted cyclic oxocarbenium ions.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Acetals / chemical synthesis
  • Acetals / chemistry
  • Catalysis
  • Cyclization
  • Hydrocarbons / chemistry
  • Indicators and Reagents
  • Ions / chemistry
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Models, Chemical*
  • Molecular Structure
  • Oxidation-Reduction

Substances

  • Acetals
  • Hydrocarbons
  • Indicators and Reagents
  • Ions
  • carbene
  • Methane