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Elektrophile Substitution und nucleophile Addition an 3,4-Dihydro-5(1H)-pyrromethenonen

Electrophilic substitution and nucleophilic addition of 3,4-dihydro-5(1H)-pyrromethenones

  • Organische Chemie Und Biochemie
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Abstract

3,4-Dihydro-5(1H)-pyrromethenones are easier attacked at themeso-position by electrophiles than 5(1H)-pyrromethenones. This is demonstrated both by aMannich-type-substitution or deuterium-exchange-experiments and by the addition of O-, S-, and N-Nucleophiles to the exocyclic double bond of the model-dihydropyrromethenone (Z)-1 under very mild reaction conditions. Applying these results to the chemistry of 2,3-dihydro-bilatrienes-abc, their chemical characteristics—especially their tautomeric behavior and their dominant C-5-selectivity towards electrophiles—become better understandable.

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Authors and Affiliations

  1. Institut für Chemie, Johannes-Kepler-Universität Linz, A-4040, Linz, Austria

    Karl Grubmayr & Gerhard Kapl

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  1. Karl Grubmayr
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  2. Gerhard Kapl
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Grubmayr, K., Kapl, G. Elektrophile Substitution und nucleophile Addition an 3,4-Dihydro-5(1H)-pyrromethenonen. Monatsh Chem 119, 605–624 (1988). https://doi.org/10.1007/BF00809213

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  • DOI: https://doi.org/10.1007/BF00809213

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