Under basic conditions, dipyrrin salts bearing alkyl and benzyl groups at the meso-position undergo deprotonation to give vinylic dipyrroles, rather than the corresponding free-base dipyrrins. The deprotonation is reversible and quantitatively returns the dipyrrinato framework under acidic conditions.
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Formation of vinylic dipyrroles by the deprotonation of meso-alkyl and meso-benzyl dipyrrin HCl salts.
J Org Chem
April 2009
Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, B3H 4J3, Canada.
Under basic conditions, dipyrrin salts bearing alkyl and benzyl groups at the meso-position undergo deprotonation to give vinylic dipyrroles, rather than the corresponding free-base dipyrrins. The deprotonation is reversible and quantitatively returns the dipyrrinato framework under acidic conditions.
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