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Updated: Jul 7, 2026

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Orbital-Overlap control in the solid-state reactivity of beta-azido-propiophenones: selective formation of
Jagadis Sankaranarayanan1, Lauren N Bort, Sarah M Mandel
1Department of Chemistry, University of Cincinnati, Cincinnati, Ohio 45221-0172, USA.
Abstract:
Solid-state photolysis of 1a,b yields selectively cis-3a,b. X-ray analysis of 1a,b reveals the molecules adopt an extended structure and as such the crystal packing arrangement consists of planar, pi-stacked molecules. The shortest intermolecular distance between adjacent N-atoms is approximately 3.76 A and would lead to formation of trans-3a,b, whereas cis-3a,b is formed by dimerization between N-atoms that are approximately 3.9 A apart. We propose that the molecular orbital alignment of the adjacent nitrenes controls the solid-state reactivity.
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