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Updated: Aug 6, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Five imide derivatives of 4-azatetracyclo[5.3.2.02,6.08,10]dodec-11-ene-3,5-dione: hydrogen bonding and
Taylor Meade1, Mitchell Fedewa1, Nicolette Owen1
1Department of Chemistry, Grand Valley State University, Allendale, MI 49401, USA.
Abstract:
The synthesis, characterization [NMR and low-resolution mass spectrometry (LR-MS)], and X-ray crystal structures of five compounds that contain a 4-azatetracyclo[5.3.2.02,6.08,10]dodec-11-ene-3,5-dione ring system are reported. The compounds vary in the identity of the substituent on the imide N atom: 2-phenyl, C17H15NO2 (I); 2-(3-methylphenyl)-, C18H17NO2 (II); 2-(4-fluorophenyl)-, C17H14FNO2 (III); 2-(2-fluorophenyl)-, C17H14FNO2 (IV); and 2-(1-methoxycarbonyl-2-phenylethyl)-, C21H21NO4 (V). All five compounds feature intermolecular C-H...O hydrogen bonds and the crystals of I-IV also contain C-H...π interactions. The crystals of fluorinated derivatives III and IV both feature C-H...F hydrogen bonds, and compound V is the only crystal to contain intramolecular C-H...O interactions.
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