352219-90-0Relevant academic research and scientific papers
3-Azabicyclo[3.3.1]nonane derivatives: VIII. Synthesis and properties of 6(7)-R-3,3-dimethyl-1,5- dinitro-3-azoniabicyclo[3.3.1]non-6-ene iodides
Shakhkeldyan,Melekhina,Atroshenko, Yu. M.,Kopyshev,Borbulevich, O. Ya.,Suponitskii, K. Yu.,Antipin, M. Yu.,Alifanova,Nikisina,Subbotin
, p. 247 - 254 (2004)
N-Alkylation of 6(7)-R-1,5-dinitro-3-methyl-3-azabicyclo[3.3.1]non-6-enes with methyl iodide afforded a series of quaternary ammonium salts whose yield depended on the solvent polarity and character of substituents located in positions 6 or 7 of substrate. The presence of electron-withdrawing groups reduced the yield of the target products compared to unsubstituted compound, whereas the electron-donor substituents increased the yield. As shown by the X-ray diffractionstudy the congormation of the substances was not changed in the course of quaternization. The DTA-TG analysis revealed that in the first stage of thermolysis the 6(7)-R-3,3-dimethyl-1,5-dinitro-3-azoniabicyclo[3.3.1]non-6- ene iodides suffer dealkylation. Two fragmentation paths of compounds synthesized under electron impact were observed: elimination either of methyl iodide or aziridinium cation.
