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Issue 9, 2017

Stereospecific photochemistry of Δ2-1,2,3-triazolines in solution and in the solid state: scope and mechanistic studies

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Abstract

The stereospecific photochemistry of ten N-aryl-substituted cis- or trans2-1,2,3-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 Δ2-1,2,3-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 Δ2-1,2,3-triazolines results in the formation of a 1,3-biradical intermediate.

Graphical abstract: Stereospecific photochemistry of Δ2-1,2,3-triazolines in solution and in the solid state: scope and mechanistic studies

Supplementary files

Article information


Submitted
20 May 2017
Accepted
18 Jul 2017
First published
19 Jul 2017

Photochem. Photobiol. Sci., 2017,16, 1458-1463
Article type
Paper

Stereospecific photochemistry of Δ2-1,2,3-triazolines in solution and in the solid state: scope and mechanistic studies

T. S. Chung, Y. Xue, A. Carranza and M. A. Garcia-Garibay, Photochem. Photobiol. Sci., 2017, 16, 1458 DOI: 10.1039/C7PP00187H

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