A mild synthetic route to α-nitroso diaryl pyrroles
Emily B Brown1, Rosinah Liandrah Gapare1, Jacob W Campbell1
1Department of Chemistry, Dalhousie University, P.O. Box 15000, Halifax, Nova Scotia, B3H 4R2, Canada. alison.thompson@dal.ca.
Abstract:
A 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.
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