6π/10π-Electrocyclization of ketene-iminium salts for the synthesis of substituted naphthylamines |
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Authors: | Emmanuelle Villedieu-Percheron Saron Catak Didier Zurwerra Roman Staiger Mathilde Lachia Alain De Mesmaeker |
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Institution: | 1. Syngenta Crop Protection AG, Crop Protection Research, Research Chemistry, Schaffhauserstrasse 101, CH-4332 Stein, Switzerland;2. Bogazici University, Chemistry Department, Bebek, 34342 Istanbul, Turkey |
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Abstract: | An intramolecular 6π/10π-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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Keywords: | Electrocyclization Ketene-iminium salts Naphthylamines DFT |
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