dc.contributor.author | Groves, Brandon R. | |
dc.contributor.author | Cameron, T. Stanley | |
dc.contributor.author | Alison, Thompson | |
dc.date.accessioned | 2018-11-01T16:58:06Z | |
dc.date.available | 2018-11-01T16:58:06Z | |
dc.date.issued | 2017 | |
dc.identifier.citation | 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 | en_US |
dc.identifier.uri | http://hdl.handle.net/10222/74924 | |
dc.description | Post-print | en_US |
dc.description.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 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. | en_US |
dc.publisher | Organic and Biomolecular Chemistry | en_US |
dc.title | Deuteration and Tautomeric Reactivity of the 1-Methyl Functionality of Free-base Dipyrrins | en_US |
dc.type | Article | en_US |