Syntheses of 3,4-Dimethylpyrrole
Kunihiro Ichimura, Susumu Ichikawa, Kazuo Imamura
Bulletin of the Chemical Society of Japan · 1976 · 10.1246/bcsj.49.1157
Abstract
Treatment of N-sulfinyl compound with 2,3-dimethylbutadiene gives a cycloadduct which affords 3,4-dimethylpyrrole in satisfactory yields by heating in a strongly alkaline methanolic solution.
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Delage-Laurin et al. reported (Liquid Crystalline Magneto-Optically Active Peralkylated Azacoronene) the modified synthesis of 3,4-dimethyl-1H-pyrrole, originally described by Ichimura et al., with three procedural changes: ethyl carbamate replaced by methyl carbamate, benzene by toluene, and steam/vacuum-distillation by extraction and silica chromatography. The reproduced yield (37%) was lower than originally reported (47.7%). Reaction scale was not stated.
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