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

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 …