Related Experiment Video
Updated: Feb 23, 2026

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Deuteration and tautomeric reactivity of the 1-methyl functionality of free-base dipyrrins
Brandon R Groves1, T Stanley Cameron, Alison Thompson
1Department of Chemistry, Dalhousie University, P.O. Box 15000, Halifax, NS, B3H 4R2, Canada. Alison.Thompson@dal.ca.
Abstract:
Regioselective reactivity of the 1-methyl group of free-base dipyrrins is explored, including discussion of tautomerism to provide exocyclic alkenyl reactivity. Deuterium is installed so as to generate dipyrrins substituted with deuterated methyl groups. Furthermore, the 1-methyl group reacts to become involved in C-C bonds involving only sp3-hybridised carbon atoms. The isolation of an elusive framework featuring a dipyrrin substituted with a pyrrole in a non-vinylogous fashion is also reported. The use of asymmetric dipyrrins featuring an electron-withdrawing group on one of the pyrrolic units results in regioselective reaction of the alpha-methyl group distal to the electron-withdrawing group.
Related Concept Videos
Basicity of Heterocyclic Aromatic Amines
Diazonium Group Substitution: –OH and –H
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
Directing and Steric Effects in Disubstituted Benzene Derivatives
Basicity of Aromatic Amines
Chirality at Nitrogen, Phosphorus, and Sulfur
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...

