Synthesis of dipyrrins bearing chirality adjacent to the conjugated skeleton - Electron-poor pyrroles exhibit dramatically reduced nucleophilicity
Beshara, Cory S.
Pearce, Beth M.
MetadataShow full item record
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.
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.