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Nucleophilic vinyl substitution Synthesis and stereochemistry of new enamino ketones of furan series

J. Kristofčák, J. Kováč, M. Dandárová, and D. Végh

Department of Organic Chemistry, Slovak Technical University, CS-812 37 Bratislava


Abstract: On nucleophilic displacement of chlorine in (E)-l-(2-furyl)-3-chloro-2-propen-1-one with primary aromatic amines and secondary aliphatic and alicyclic amines enamino ketones have been obtained. While the products with secondary amines retained the original E configuration of the molecule, the configuration of the products with aromatic primary amines was changed totally. Alternative methods for the preparation of some enamino ketones, utilizing the reactions of 2-acetylfuran and furfurylideneacetone with dimethylformamide dimethyl acetal and Gold salt, respectively, are presented. Stereochemistry of the prepared enamino ketones has been studied by 1H NMR spectroscopy.

Full paper in Portable Document Format: 405a665.pdf


Chemical Papers 40 (5) 665–672 (1986)

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