Issue 37, 2017

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

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

Supplementary files

Article information

Article type
Paper
Submitted
24 Maijs 2017
Accepted
07 Sept. 2017
First published
13 Sept. 2017

Org. Biomol. Chem., 2017,15, 7925-7935

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, 15, 7925 DOI: 10.1039/C7OB01278K

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