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An NMR study of sequential intermediates and collateral products in the conversion of 1,3,6,8-tetraazatricyclo[4.4.1.13,8]dodecane (TATD) to 1,3,6,8-tetraazatricyclo[4.3.1.13,8]undecane (TATU)

✍ Scribed by Augusto Rivera; Martín E. Núñez; Eliseo Avella; Jaime Ríos-Motta

Publisher
Elsevier Science
Year
2008
Tongue
French
Weight
429 KB
Volume
49
Category
Article
ISSN
0040-4039

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✦ Synopsis

In situ 1 H nuclear magnetic resonance spectroscopy was used to investigate the processes that occur during the synthesis of 1,3,6,8tetraazatricyclo[4.3.1.1 3,8 ]undecane (TATU). NMR analysis showed a reaction mixture containing more than one compound. The production of these intermediates and collateral products was rationally supported by a careful 1 H NMR monitoring study. We characterized 1,3,5-triazabicyclo[3.2.1]octane (TABO, 4) and 3-(2-aminoethyl)-1,3,5-triazabicyclo[3.2.1]octane (AETABO, 7) by 1 H and 13 C NMR in D 2 O solution inside the NMR sample tube, as an intermediate and collateral product of the reaction, respectively. Further, a reaction of 1,3,6,8-tetraazatricyclo[4.4.1.1 3,8 ]dodecane (TATD) with 15 N-labeled ammonium chloride was carried out. The 15 N NMR and GC-MS experiments indicated that 15 N was incorporated into TATU, TABO, and urotropine.

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