S. S. Koval’skaya, N. Kozlov
Jun 1, 2000
Citations
0
Influential Citations
0
Citations
Journal
Russian Journal of Electrochemistry
Abstract
Abstractcis-4,4,6-Trimethylbicyclo [3.1.1]heptan-2-one (verbanone) in Mannich condensation with paraformaldehyde and dimethylamine adds an aminomethyl fragment at the most sterically accessible carbon C3 to form an equatorial isomer. The latter treated with sulfuric acid in acetonitrile affords a mixture of two 2-azalactams, 4-(dimethylantinomethyl)-5,7,7-trimethyl-2-azabicyclo[4.1.1]octan-3-one and its deamination product 4-methylene-5,5,7-trimethyl-2-azabicyclo[4.1.1]octan-3-one in 9:1 ratio. Z-isomer of amino oxime prepared by oximation of 3-(dimethylaminomethyl)verbanone under similar conditions affords a mixture of two 3-azalactams, 4-(dimethylaminomethyl)-5,7,7-trimethyl-3-azabicyclo[4.1.1]octan-2-one and its deamination product in 5:3 ratio. Mannich bases prepared from verbanone and its oxime were converted into the respective iodomethylates. Deamination of the latter results in a single product, α,\-unsaturated ketone 3-methyleneverbanone.