J. Richman, H. Simmons
1974
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0
Influential Citations
16
Citations
Journal
Tetrahedron
Abstract
Abstract The highly symmetrical 1,4,7,10-tetraazatetracyclo[5.5.1.0 4,13 .0 10,13 ]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.