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Updated: Oct 14, 2025

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Phosphorus mediated imidazolinium to oxazolium ring rearrangement
Deependra Bawari1, Solomon Volodarsky1, Yael Ginzburg1
1School of Chemistry, Raymond and Beverly Sackler Faculty of Exact Sciences, Tel Aviv University, Tel Aviv 69978, Israel. rdobrove@tau.ac.il.
Abstract:
An unexpected rearrangement occurred when an imidazolinium based OCO pincer-type ligand (1) reacted with PCl3 producing a chlorophosphine with a pendant oxazolium "arm" (3). The mechanism of this rearrangement was studied both experimentally and by density functional theory (DFT) computations. The deprotonation of 3 led to further unexpected results.
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