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Updated: Sep 17, 2025
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Photocyclization of 8-Aryloxybenzo[e][1,2,4]triazines Revisited: Unambiguous Structural Assignment of Planar Blatter
Hemant K Singh1, Sławomir Kaźmierski1, Piotr Kaszyński1,2,3
1Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, 90-363 Łódź, Poland.
Abstract:
The recent discovery of a photo-Smiles rearrangement and the development of effective analytical methods prompted structural investigation of the previously reported planar Blatter radicals obtained by photocyclization of 8-aryloxy-3-phenylbenzo[e][1,2,4]triazines. Thus, seven freshly prepared radicals were cleanly converted to their leuco forms and analyzed by 2D correlation 1H NMR methods (COSY, TOCSY, and ROSEY). Results demonstrate that all investigated 8-aryloxy-3-phenylbenzo[e][1,2,4]triazines undergo photocyclization with Smiles rearrangement and exclusive formation of a single rearranged product. This work corrects the previously reported structural assignment and DFT data of planar Blatter radicals and further demonstrates the generality of this new variation of the photo-Smiles rearrangement.
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