Brown, Emily B.Gapare, Rosinah LiandrahCampbell, Jacob W.Alkaş, AdilSequeira, SteveHilborn, James W.Greening, Sarah M.Robertson, Katherine N.Thompson, Alison2024-09-102024-09-102024Published Version: Brown, E. B., Gapare, R. L., Campbell, J. W., Alkaş, A., Sequeira, S., Hilborn, J. W., ... & Thompson, A. (2024). A mild synthetic route to α-nitroso diaryl pyrroles. Organic & Biomolecular Chemistry, 22(30), 6122-6128.http://hdl.handle.net/10222/84593A new synthetic method to access α-nitroso pyrroles is presented. This method utilises the nitrosonium salt NOBF4, enabling short reaction times (<10 minutes) and avoiding the harsh acidic conditions usually associated with pyrrole nitrosation. Application of this procedure to diarylated pyrroles yielded several novel nitroso-pyrroles. Modifications to the method, through exclusion of air and inclusion of a mild base, allowed for the nitrosation of pyrroles bearing aryl groups substituted with electron-donating groups. Attempts to nitrosylate pyrroles bearing alkyl substituents resulted in the formation of a dimeric material composed of a pyrrolic unit and a 2-hydroxyimino-protected 1,5-dihydro-2H-pyrrol-2-one.Text