A. Genaev, V. Sokolenko, G. E. Sal’nikov
Jul 1, 2002
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Journal
Russian Journal of Organic Chemistry
Abstract
According to the 1H NMR data, the reaction of equimolar amounts of 3,7-dimethylenebicyclo[3.3.1]nonane with trifluoromethanesulfonic acid in CD2Cl2 leads to formation of 3-methyl-1-adamantyl trifluoromethanesulfonate. Further addition of trifluoromethanesulfonic acid promotes partial dissociation of 3-methyl-1-adamantyl trifluoromethanesulfonate into 3-methyladamantyl cation and trifluoromethanesulfonate anion, and the cation undergoes fast pericyclic rearrangement involving migration of bridgehead hydrogen atoms to the cationic center.