Title

An Anomalous Dipyrrole Product from Attempted Synthesis of a Tetraarylporphyrin

Document Type

Article

Publication Date

12-1-1988

Abstract

Heating of o-acetoxybenzaldehyde with pyrrole in hot acetic acid under Adler/Rothemund conditions yields a bright red (γmax 515 nm) dipyrrolic compound and only minor quantities of the expected tetraarylporphyrin. Using NMR, mass spectrometry, and X-ray crystallography, we show the red material to be the dibenzofuranylpyrromethene 3. A mechanism for the formation of this material is presented. © 1988, American Chemical Society. All rights reserved.

Publication Source (Journal or Book title)

Journal of Organic Chemistry

First Page

5847

Last Page

5849

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