Volume 20, Issue 22
Heterocyclic Compounds
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ChemInform Abstract: An Anomalous Dipyrrole Product from Attempted Synthesis of a Tetraarylporphyrin.

J. A. S. CAVALEIRO

J. A. S. CAVALEIRO

Dep. Chem., Univ., 3800-Aveiro, Portugal

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M. F. P. N. CONDESSO

M. F. P. N. CONDESSO

Dep. Chem., Univ., 3800-Aveiro, Portugal

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M. M. OLMSTEAD

M. M. OLMSTEAD

Dep. Chem., Univ., 3800-Aveiro, Portugal

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D. E. ORAM

D. E. ORAM

Dep. Chem., Univ., 3800-Aveiro, Portugal

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K. M. SNOW

K. M. SNOW

Dep. Chem., Univ., 3800-Aveiro, Portugal

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K. M. SMITH

K. M. SMITH

Dep. Chem., Univ., 3800-Aveiro, Portugal

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First published: May 30, 1989

Abstract

Reaction of o-acetoxybenzaldehyde (I) with pyrrole (II) in refluxing acetic acid gives a mixture of the dibenzofuranylpyrromethene (IIIa) and the deacetylation product (IIIb).

ChemInform Abstract

Reaction of o-acetoxybenzaldehyde (I) with pyrrole (II) in refluxing acetic acid gives a mixture of the dibenzofuranylpyrromethene (IIIa) and the deacetylation product (IIIb). These are converted into each other as shown in the reaction scheme. The aldehyde (I) and pyrrole (II) form only approximately 1% of (III), when the reaction is performed in the presence of zinc(II) acetate. (Mechanism, crystal data of (IIIa): orthorhombic, space group P212121, Z = 8).

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