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Updated: Jul 6, 2026

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
(1-Pyridinio)perfluorophenacylide: a new stable pyridinium ylide in the enol form
1Department of Chemistry, Faculty of Science, Ochanomizu University, Bunkyo-ku, Tokyo 112-8610, Japan. yamada.shinji@ocha.ac.jp
Abstract:
The title compound, C(13)H(6)F(5)NO, exists in the enol form and adopts the E configuration about the enol double bond. It is the first example of an enol-type pyridinium ylide. The enol structure was unambiguously determined on the basis of the significantly longer C-O bond and shorter C-C bond. Intramolecular C-H...O and C-H...F hydrogen bonds are responsible for promotion of the enol form and for the stability of this compound.
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Electrophilic Addition to Alkynes: Halogenation
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.

