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Photochemically Induced Aryl Azide Rearrangement: Solution NMR Spectroscopic Identification of the Rearrangement Product

Journal article
Authors Hanna Andersson
Jürgen Gräfenstein
Minoru Isobe
Mate Erdelyi
Magne O. Sydnes
Published in Journal of Organic Chemistry
Volume 82
Issue 3
Pages 1812-1816
ISSN 0022-3263
Publication year 2017
Published at Swedish NMR Centre at Göteborg University
Department of Chemistry and Molecular Biology
Pages 1812-1816
Language en
Subject categories Spectroscopy, Quantum chemistry, Organic Chemistry, Chemical Sciences


Photolysis of ethyl 3-azido-4,6-difluorobenzoate at room temperature in the presence of oxygen results in the regioselective formation of ethyl 5,7-difluoro-4-azaspiro[2.4]hepta-1,4,6-triene-1-carboxylate, presumably via the corresponding ketenimine intermediate which undergoes a photochemical four-electron electrocyclization followed by a rearrangement. The photorearrangement product was identified by multinuclear solution NMR spectroscopic techniques supported by DFT calculations.

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