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Updated: Jul 5, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
The (±)-5-Aza[1.0]triblattane Skeleton via Azetine Cycloaddition
Chuyi Su1, Madeleine A Dallaston1, Renée D Watson1
1School of Chemistry and Molecular Biosciences, University of Queensland, Brisbane, 4072 Queensland Australia.
Abstract:
The first synthesis of the 5-aza[1.0]triblattane skeleton was achieved through a [4 + 2] cycloaddition approach using a suitably protected azetine and cyclopentadiene. A series of azetines were synthesized to explore both stability and suitable N-protection. The key step following cycloaddition utilized a noninitiated protonated aminyl radical cyclization to install the final 5-azatriblattane bond, but it was found to be considerably more unstable than the 6-aza isomer under acidic conditions.
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