120893-33-6Relevant academic research and scientific papers
Adamantane-2-spiro-3'-diazirine in reactions with protic and aprotic acids
Isaev, S. D.,Zhalnina, G. G.,Murzinova, Z. N.,Lastovenko, S. I.,Yurchenko, A. G.
, p. 126 - 131 (2007/10/02)
During the action of strong protic acids on adamantane-2-spiro-3'-diazirine addition of the proton is accompanied by the elimination of a molecule of nitrogen and the formation of the intermediate 2-adamantyl cation.In the presence of nucleophiles the latter is converted into the corresponding 2-substituted derivatives of adamantane.Lewis acids promote isomerization of the cyclic diazirine to the linear diazo compound, and the main reaction product is adamantanone azine.Trifluoroacetic acid and bromine react by both mechanisms simultaneously. (In the latter case Br+ plays the role of the proton in the first stage.)
