In methanol solution, 1,4,7-tri(pent-4'-yn-1'-yl)-1,4,7-triazacyclononane undergoes an intramolecular hydroamination reaction to form an azoniaspiro[4.8]tridecane cation, 1-methylidene-8,11-di(pent-4'-yn-1'-yl)-8,11-diaza-5-azoniaspiro[4.8] tridecane. The azoniaspiro[4.8]tridecane cation, as its tetraphenylborate salt, has been characterized spectroscopically in solution and by X-ray studies in the solid state. Reactions of the azoniaspiro[4.8]tridecane that lead to other products are also discussed.
Baker, M., Brown, D., Skelton, B., & White, A. (2000). Intramolecular Hydroamination of 1,4,7-Tri(pent-4' -yn-1' -yl)-1.4.7-triazacyclononane: Formation of an Azoniaspiro [4.8] tridecane. Australian Journal of Chemistry, 53(2000), 791-797. https://doi.org/10.1071/CH00123