Homoenolization of 1,3,3-trimethylbicyclo[2.2.1]heptan-2-one in perdeuterated tert-butyl alcohol. Evidence that the medium potassium tert-butoxide – tert-butyl alcohol is unstable at elevated temperatures Academic Article uri icon

  •  
  • Overview
  •  
  • Research
  •  
  • Identity
  •  
  • Additional Document Info
  •  
  • View All
  •  

abstract

  • Homoenolization of 1,3,3-trimethylbicyclo[2.2.1]heptan-2-one (1) (fenchone) in potassium tert-butoxide – tert-butyl alcohol-O-d and perdeuterated potassium tert-butoxide – tert-butyl alcohol at 220 °C established that there is significant deterioration of the medium and dilution of the deuterium pool. We show that the major pathway of deterioration of the medium and dilution of the pool involves formation of isobutene by elimination of water from the alcohol. Exchange data already accumulated in the literature are used to support our view that the elimination also occurs at 185 °C, the temperature commonly used to homoenolize ketones.

publication date

  • February 1, 1985