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Photochemically Induced Aryl Azide Rearrangement: Solution NMR Spectroscopic Identification of the Rearrangement Product
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Organisk kemi. University of Gothenburg, SE-412 96 Gothenburg, Sweden.ORCID-id: 0000-0003-3798-3322
National Sun Yat-Sen University, Kaohsiung, Taiwan.
National Sun Yat-Sen University, Kaohsiung, Taiwan.ORCID-id: 0000-0002-5244-3300
University of Gothenburg, SE-412 96 Gothenburg, Sweden; The Swedish NMR Centre, SE-413 96 Gothenburg, Sweden.ORCID-id: 0000-0003-0359-5970
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2017 (engelsk)Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 82, nr 3, s. 1812-1816Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

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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2017. Vol. 82, nr 3, s. 1812-1816
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URN: urn:nbn:se:uu:diva-346687DOI: 10.1021/acs.joc.6b02555PubMedID: 28068094OAI: oai:DiVA.org:uu-346687DiVA, id: diva2:1191835
Tilgjengelig fra: 2018-03-20 Laget: 2018-03-20 Sist oppdatert: 2018-04-05bibliografisk kontrollert

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