Synthesis of dipyrrins bearing chirality adjacent to the conjugated skeleton - Electron-poor pyrroles exhibit dramatically reduced nucleophilicity
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Date
2008-10Author
Beshara, Cory S.
Pearce, Beth M.
Thompson, Alison
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Show full item recordAbstract
With the aim of furthering our investigations into the asymmetric complexation of dipyrrinato
ligands, a dipyrrin bearing a stereogenic centre directly adjacent to the conjugated skeleton was
synthesized. The electron- withdrawing nature of the chiral 4-(2,2,2-trifluoro-1-hydroxyethyl)-
substituent significantly reduced the nucleophilicity of corresponding pyrroles, such that
2,2'-symmetrically substituted bis(dipyrrin)s bearing this motif were inaccessible. Furthermore,
solutions of mononuclear dipyrrinato complexes were found to be less stable to acid-catalyzed
decomplexation than the corresponding dinuclear complexes.
Citation
Beshara, Cory S., Beth M. Pearce, and Alison Thompson. 2008. "Synthesis of dipyrrins bearing chirality adjacent to the conjugated skeleton - Electron-poor
pyrroles exhibit dramatically reduced nucleophilicity." Canadian Journal of Chemistry-Revue Canadienne De Chimie 86(10): 951-957.