Journal
TETRAHEDRON LETTERS
Volume 52, Issue 2, Pages 341-345Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.11.073
Keywords
2-Vinyl-2-diazocarbonyl compounds; cis-trans-Stereochemistry; Pyrazoles; Pyridazines; Phosphazines; 1,5-Electrocyclizations; Diaza-Wittig reactions
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3-(Trifluoromethyl)-substituted (F) 2-vinyl-2-diazocarbonyl compounds, having cis-relationship of functional groups (AlkO(2)C. 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 AlkO(2)C and CN2 groups. (C) 2010 Elsevier Ltd. All rights reserved.
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