1,4,7,10-tetraazatetracyclo[5.5.1.04,13.010,13]tridecane: Degenerate rearrangement of its conjugate acid

Jack E. Richman, Howard E. Simmons

Research output: Contribution to journalArticle

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Abstract

The highly symmetrical 1,4,7,10-tetraazatetracyclo[5.5.1.04,13.010,13]tridecane (1) has been synthesized by two methods. The proton NMR spectrum of 1 is analyzed. The cyclic tetraaminomethane derivative undergoes a remarkable series of degenerate prototropic and conformational equilibria. The temperature dependence of the proton NMR spectra of 1 and its conjugate acid 3 are interpreted in terms of a large rate enhancement of intramolecular nucleophilic addition to guanidinium ion 3 (ring-chain tautomerism) compared to its acyclic counterpart.

Original languageEnglish (US)
Pages (from-to)1769-1774
Number of pages6
JournalTetrahedron
Volume30
Issue number13
DOIs
StatePublished - 1974

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