THE DEAMINATION OF ALICYCLIC α-AMINOKETONES

Abstract

The deamination of α-aminocyclohexanones has been shown to give cyclopentane carboxylic acids, bicyclo[3,1,0]hexane-2-ones, and 2-methyl-2-cyclopentene-1-ones. Deamination of 3-endo-aminocamphor gave cyclocamphanone, 6-isopropenyl-6-methyl-2-cyclohexen-1-one, and 6- (1′-hydroxy-1′-methylethyl)-6-methyl-2-cyclohexen-1-one.The formation of bicyclo[3,1,0]hexane by deamination of cyclohexylamine is reported for the first time. The difference between the products from it and bornylamine and those from the corresponding α-aminoketones are rationalized on the basis of the amount of C—C participation in the corresponding carbonium ions.