Chemistry of Heterocyclic Compounds p. 1292 - 1298 (1997)
Update date:2022-08-03
Topics:
Zubarev
Gurskaya
Zavodnik
Ostrovskii
The cycloaddition of dimethylammonium azide to the nitrile groups of 2-cyanoethyl derivatives of CH-, OH-, and NH-acids leads to open-chain branched structures containing terminal NH-tetrazolyl groups. An x-ray diffraction structural analysis of tris[2-(5-tetrazolyl)ethyl]nitromethane revealed steric access of the equivalent NH-tetrazolyl rings of the branched system. In going from the branched nitrile substrates to the corresponding tetrazoles, the PMR spectra show a breakdown in the resolution of the multiplet components, which had not been observed previously for monocyclic 5-substituted tetrazoles. A dependence was found for the 13C NMR chemical shifts on the pKa values, reflecting the NH-addity of the branched polycyclic tetrazoles in water.
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