Stereochemistry and reactivity of F- and H-vinyldiazocarbonyl compounds and their phosphazines: synthesis of pyrazoles and pyridazines |
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Authors: | Murat B. SupurgibekovValerija M. Zakharova Jochim SielerValerij A. Nikolaev |
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Affiliation: | a Saint-Petersburg State University, University Prosp. 26, St.-Petersburg 198504, Russia b Universität Leipzig, Institut für Anorganische Chemie, Johannisallee 29, D-04103 Leipzig, Germany |
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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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Keywords: | 2-Vinyl-2-diazocarbonyl compounds cis-trans-Stereochemistry Pyrazoles Pyridazines Phosphazines 1,5-Electrocyclizations Diaza-Wittig reactions |
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