期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 16, 期 47, 页码 9211-9217出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8ob02721h
关键词
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资金
- National Natural Science Foundation of China [21502076]
- Natural Science Foundation of Jiangxi province [20161BAB213068]
- Outstanding Young Talents Scheme of Jiangxi Province [20171BCB23039]
The transformation of hydroximoyl fluorides to nitrile oxides for [3 + 2]-cycloaddition with alkynes has been achieved for the first time. The hydroximoyl fluorides used in this work appeared to be not stable, which was proved by a series of experiments. A DFT calculation was performed to better understand the properties of hydroximoyl fluorides. Although not stable, the hydroximoyl fluorides could be successfully converted to the corresponding nitrile oxides for in situ [3 + 2]-cycloaddition with alkynes to yield the iso-xazoles. Furthermore, it was feasible to conduct [3 + 2]-cycloaddition reaction without purification after the synthesis of hydroximoyl fluorides from gem-difluoroalkenes. By investigating a class of interesting yet previously rarely explored fluorinated compounds, this work sheds new light on the stability and reactivity of a C-F bond on a C=N double bond.
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