Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5268173 | Tetrahedron Letters | 2011 | 5 Pages |
Abstract
3-(Trifluoromethyl)-substituted (F) 2-vinyl-2-diazocarbonyl compounds, having cis-relationship of functional groups (AlkO2C, CN2), do not undergo 1,5-electrocyclization, but readily take part in the tandem Staudinger-diaza-Wittig reactions to produce trifluoromethyl-substituted pyridazines, whereas their non-fluorinated analogs (H), with trans-configuration, easily cyclize to pyrazoles, but remain intact under Staudinger-diaza-Wittig reaction conditions. The difference in the reactivity of H- and F-vinyldiazoketones, vinyldiazoacetates, and derived phosphazines is apparently caused by the different stereochemical arrangements of the AlkO2C and CN2 groups.
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Murat B. Supurgibekov, Valerija M. Zakharova, Jochim Sieler, Valerij A. Nikolaev,