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Deuteration and tautomeric reactivity of the 1-methyl functionality of free-base dipyrrins

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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.

Graphical abstract: Deuteration and tautomeric reactivity of the 1-methyl functionality of free-base dipyrrins

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Publication details

The article was received on 24 May 2017, accepted on 07 Sep 2017 and first published on 13 Sep 2017


Article type: Paper
DOI: 10.1039/C7OB01278K
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Deuteration and tautomeric reactivity of the 1-methyl functionality of free-base dipyrrins

    B. R. Groves, T. S. Cameron and A. Thompson, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB01278K

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