Deuteration and Tautomeric Reactivity of the 1-Methyl Functionality of Free-base Dipyrrins
Groves, Brandon R.
Cameron, T. Stanley
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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 such 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.
Groves, B. R., Cameron, T. S., & Thompson, A. (2017). Deuteration and tautomeric reactivity of the 1-methyl functionality of free-base dipyrrins. Organic & biomolecular chemistry, 15(37), 7925-7935. DOI: 10.1039/C7OB01278K