TY - JOUR
T1 - 1,4,7,10-tetraazatetracyclo[5.5.1.04,13.010,13]tridecane
T2 - Degenerate rearrangement of its conjugate acid
AU - Richman, Jack E.
AU - Simmons, Howard E.
PY - 1974
Y1 - 1974
N2 - 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.
AB - 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.
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U2 - 10.1016/S0040-4020(01)97311-9
DO - 10.1016/S0040-4020(01)97311-9
M3 - Article
AN - SCOPUS:0011718616
SN - 0040-4020
VL - 30
SP - 1769
EP - 1774
JO - Tetrahedron
JF - Tetrahedron
IS - 13
ER -