Stereospecific photochemistry of Δ 2 -1,2,3-triazolines in solution and in the solid state: scope and mechanistic studies

The stereospecific photochemistry of ten N-aryl-substituted cis- or trans-Δ -1,2,3-triazolines to form the corresponding cis- or trans-aziridines was investigated both in solution and in the solid-state. We found that photochemical reactions in the solid state are more stereospecific than in solutio...

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Published inPhotochemical & photobiological sciences Vol. 16; no. 9; p. 1458
Main Authors Chung, Tim S, Xue, Yang, Carranza, Alberto, Garcia-Garibay, Miguel A
Format Journal Article
LanguageEnglish
Published England 13.09.2017
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Summary:The stereospecific photochemistry of ten N-aryl-substituted cis- or trans-Δ -1,2,3-triazolines to form the corresponding cis- or trans-aziridines was investigated both in solution and in the solid-state. We found that photochemical reactions in the solid state are more stereospecific than in solution for the 8 crystalline Δ -1,2,3-triazolines. Additionally, triplet sensitization for some triazolines results in triplet biradicals, which provide the more thermodynamically favored trans-aziridine regardless of the starting triazoline stereochemistry. Product analyses as a function of temperature and solvent polarity suggest that the electronic excitation of the Δ -1,2,3-triazolines results in the formation of a 1,3-biradical intermediate.
ISSN:1474-9092