Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 4, Pages 1868-1879Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo202477h
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- NRW Graduate School of Chemistry Munster
- Deutsche Forschungsgemeinschaft (DFG, Bad Godesberg)
- Fonds der Chemischen Industrie (Frankfurt)
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1-Azapenta-1,4-diene-3-ols 4a-m are easily accessible from 1-azapenta-1,4-dien-3-ones 3a-i and organo-lithium compounds. Treatment of the compounds 4a-m with strong acid (triflic acid) generates 1-azapentadienyl cations in situ upon protonation at the hydroxyl oxygen atom and subsequent water elimination. The intermediate cations undergo facile 4 pi-electrocyclization under ambient condition to give diversely substituted pyrroles 6a-m in moderate to good yield. The product pyrrole 6k could be characterized by X-ray diffraction. Quantum chemical calculations were performed to elucidate the mechanism of this reaction with respect to starting compounds, transition states, and products. They support the proposed mechanism of a 4 pi-conrotatory Mobius-type electrocyclic ring-closure reaction.
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