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Reactivite ambidente de l'anion imidazolate vis-a-vis d'un electrophile aromatique

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
23
Issue
40
Identifiers
DOI: 10.1016/s0040-4039(00)88352-5
Disciplines
  • Physics

Abstract

Abstract The reaction of 1,3,5-trinitrobenzene (TNB) with imidazolide ion (Im -) provides the first example of the ambifunctional nucleophilic reactivity of this anion towards an aromatic electrophile. The N-adduct 1 is formed under kinetic control but the C-adduct 2 is the thermodynamically stable product. The N,C-diadduct 3 is also observed.

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