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Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron
Published on: August 12, 2019
Trapping of the putative cationic intermediate in the Morin rearrangement with carbon nucleophiles
J D Freed1, D J Hart, N A Magomedov
1Department of Chemistry, Ohio State University, 100 W. 18th Avenue, Columbus, Ohio 43210, USA.
Abstract:
This paper presents reactions in which the putative cationic intermediate in the Morin rearrangement is trapped by aromatic carbon nucleophiles (indoles and furans). For example, reaction of sulfoxide 27 with trifluoroacetic acid in chloroform provides, among other products, indole 29 and indoline 30. The indoline was shown to be in equilibrium with the nine-membered ring bridged indole 31. Other examples of Morin rearrangement-trapping reactions are presented, and mechanisms for these transformations are proposed.
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