Photochemically Induced Aryl Azide Rearrangement: Solution NMR Spectroscopic Identification of the Rearrangement Product
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- 作者：Hanna AnderssonJürgen Gräfenstein ; Minoru Isobe ; Máté ErdélyiMagne O. Sydnes
- 刊名：Journal of Organic Chemistry
- 出版年：2017
- 出版时间：February 3, 2017
- 年：2017
- 卷：82
- 期：3
- 页码：1812-1816
- 全文大小：384K
- ISSN：1520-6904
文摘
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.