Title

Anomalous electrophilic substitution reactions in 3,3′-linked dipyrromethanes

Document Type

Article

Publication Date

1-1-1996

Abstract

The 3,3′-linked dipyrromethane 5 was synthesized by the self-condensation of hydroxymethylpyrrole 4; along with 5, a minor by-product was the novel tripyrrane 7. Vilsmeier formylation of 5 unexpectedly afforded the formylpyrrole 6 instead of the diformyldipyrromethane 8. Likewise, acylation of 5 gave acetylpyrrole 9 as the major product. A mechanism is proposed for this novel 3,3′-dipyrromethane acylation(formylation)/fragmentation reaction.

Publication Source (Journal or Book title)

Heterocyclic Communications

First Page

9

Last Page

12

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