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A novel ambident reactivity of azolylacroleins

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
63
Issue
22
Identifiers
DOI: 10.1016/j.tet.2007.03.098
Keywords
  • Azolyltriene
  • Wittig Reaction
  • Phosphorane
  • Ab Initio Calculation

Abstract

Abstract Reaction of azolylacroleins with phosphoranes bearing a conjugated double bond was found to yield either azolyltrienes in a Wittig reaction, or to undergo cyclization to a dihydrobenzene containing the azole substituent. Transformation with an aza-Wittig reagent gave tetrazolylpyridines. The ambident reactivity was found to be dependent on the substituent of the phosphorane, which was rationalized by ab initio (DFT) calculation of the atomic charges of the reaction centres.

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