1,3- and 1,2-Carbo-migration of 2-vinylbicyclo[2.2.2]octenols: facile and concise synthesis of bicyclo[4.2.2]/[3.2.2] skeleton by two/one-carbon ring expansion

Chem Asian J. 2008 Sep 1;3(8-9):1422-9. doi: 10.1002/asia.200800113.

Abstract

The synthesis of a series of bicyclo[4.2.2]octenones and bicyclo[3.2.2]heptenones by 1,3- or 1,2-migration reaction from 2-vinylbicyclo[2.2.2]octenols is reported. These ring-expansion reactions were accomplished under basic or neutral conditions. Whether 1,3- or 1,2-migration takes place depends on endo- or exocyclic olefin displacement in the substrates.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry
  • Anions / chemistry
  • Bridged Bicyclo Compounds / chemical synthesis*
  • Bridged Bicyclo Compounds / chemistry
  • Carbon / chemistry*
  • Furans / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Octanes / chemistry*
  • Vinyl Compounds / chemical synthesis*
  • Vinyl Compounds / chemistry

Substances

  • Alkenes
  • Anions
  • Bridged Bicyclo Compounds
  • Furans
  • Octanes
  • Vinyl Compounds
  • Carbon
  • octane