Nonaromatic corroles: regioselectivity of electrophilic substitution.
Ring contraction of nickel meso-tetraarylporphyrins produced nonaromatic divalent corroles bearing a benzoyloxy function. We investigated their reactivity under electrophilic conditions: formylation, halogenation, nitration. We also found that the benzoate function could be eliminated to afford deoxocorroles, and we tested the formylation and nitration in this deoxo series. These corroles were generally very stable under the reaction conditions, and in both series, the directly bonded pyrroles were the most reactive. The nitration reaction produced a series of corrole dimers via electron transfer initiated coupling.
Ruppert
Romain
R
Institut de Chimie, UMR CNRS 7177, Université Louis Pasteur, 1 rue Blaise Pascal, 67000 Strasbourg, France.
Jeandon
Christophe
C
Callot
Henry J
HJ