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

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 bec...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2017-09, Vol.15 (37), p.7925-7935
Main Authors: Groves, Brandon R, Cameron, T Stanley, Thompson, Alison
Format: Article
Language:English
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Summary: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 sp -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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob01278k