期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2019, 期 2-3, 页码 342-350出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201800143
关键词
Alkynes; Nitrogen heterocycles; Carbenes; Reaction mechanisms
资金
- University of Versailles St-Quentin-en-Yvelines
- University Paris-Saclay
- Centre National de la Recherche Scientifique (CNRS)
- l' Ecole polytechnique
This article focuses on the dehydration of -hydroxy-tetrazoles, leading to tetraazafulvenes and then to vinylic carbenes that rearrange into ethynyl moieties through the Fritsch-Buttenberg-Wiechell rearrangement. Each step of this sequence was scrutinized, either by examination of the substrate and/or dehydrating agent scope, or through AM1 calculations, in order to understand the limiting step of this process. This underrated transformation appears to be a viable alternative to existing methods used for transforming aldehydes into alkynes.
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