| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5270503 | Tetrahedron Letters | 2014 | 4 Pages |
Abstract
An intramolecular 6Ï/10Ï-electrocyclization from ketene-iminium salts was developed for the preparation of naphthylamines. Various substituents on the nitrogen, on the aromatic ring, and on the olefin were studied. Tricyclic skeletons were obtained in few steps and good overall yields. The electrocyclization of ketene-iminium salts has been computationally explored by means of DFT calculations and their activation barriers were compared to the parent triene as well as the corresponding dienyl allenes and dienyl ketenes. Electrocyclizations for ketene-iminium salts were shown to be highly exergonic and have much smaller barriers to activation.
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Emmanuelle Villedieu-Percheron, Saron Catak, Didier Zurwerra, Roman Staiger, Mathilde Lachia, Alain De Mesmaeker,