ChemInform Abstract: Pyrolytic Generation and Rearrangement of N-Substituted 1,2- Didehydrocarbazoles.
Abstract
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ChemInform Abstract
Flash vacuum pyrolysis of a series of anhydrides leads to intermediate 1,2-didehydrocarbazoles which mainly undergo ring expansion, dealkylation, and cyclization reactions. Ring contractions of the aryne system to exocyclic carbenes are not observed. The benzyl derivative (XI) gives a complex mixture in which products derived from initial N-Bn cleavage predominate (bibenzyl, benzaldehyde, benzyl alcohol, carbazole). The trace product (XII) is probably formed by an intramolecular cycloaddition.
