Work

Photocyclization of 8-Aryloxybenzo[e][1,2,4]triazines Revisited: Unambiguous Structural Assignment of Planar Blatter Radicals by Correlation NMR Spectroscopy

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide 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 1 H 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.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.5c00741

Authors: Hemant K. Singh, Sławomir Kaźmierski, Piotr Kaszyński

Institutions: Centrum Badań Molekularnych i Makromolekularnych Polskiej Akademii Nauk, Polish Academy of Sciences, Middle Tennessee State University, University of Łódź

Language: English

Topic: Chemical Reactions and Mechanisms

Subfield: Physical and Theoretical Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funder: Narodowe Centrum Nauki