Stereochemistry and reactivity of F-and H-vinyldiazocarbonyl compounds and their phosphazines: synthesis of pyrazoles and pyridazines

MB Supurgibekov, VM Zakharova, J Sieler…

Index: Supurgibekov, Murat B.; Zakharova, Valerija M.; Sieler, Jochim; Nikolaev, Valerij A. Tetrahedron Letters, 2011 , vol. 52, # 2 p. 341 - 345

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Citation Number: 23

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 ...