Monatshefte fur Chemie p. 605 - 624 (1988)
Update date:2022-07-31
Topics:
Grubmayr, Karl
Kapl, Gerhard
3,4-Dihydro-5(1H)-pyrromethenones are easier attacked at the meso-position by electrophiles than 5(1H)-pyrromethenones.This is demonstrated both by a Mannich-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 behaviour and their dominant C-5-selectivity towards electrophiles - become better understandable. - Keywords: 3,4-Dihydro-5(1H)-pyrromethenones; 5(1H)-Pyrromethenones; 2,3-Dihydro-bilatrienes-abc; Electrophilic substitution; Nucleophilic addition
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