Juergen O. Metzger et.al.: Lewis acid-induced additions to unsaturated fatty compounds. Part 4. Synthesis of cyclopentenones from Friedel-Crafts acylation products of unsaturated fatty compounds with a,b-unsaturated acyl chlorides

Author(s): Juergen O. Metzger, Ursula Biermann

Title: Lewis acid-induced additions to unsaturated fatty compounds. Part 4. Synthesis of cyclopentenones from Friedel-Crafts acylation products of unsaturated fatty compounds with a,b-unsaturated acyl chlorides

Date of Upload: 1998

Article: Fett/Lipid (1998), 100(1), 2-6, Department of Chemistry, University of Oldenburg, Carl-von-Ossietzky-Str. 9-11, 26129 Oldenburg, Germany

Keywords: Alicyclic Compounds, Friedel-Crafts reaction, Fatty acids, reactions, sustainable development, renewable feedstock, vegetable oil, plant oil,

Abstract:
The EtAlCl2-induced Friedel-Crafts acylation of unsatd. fatty compds. such as oleic acid, Me oleate, and 10-undecenoic acid and, furthermore, of 1-octene with a,b-unsatd. acyl chlorides, e.g. crotonyl chloride and acrylic chloride, gave the corresponding allyl vinyl ketones. Nazarov cyclizations of the acylation products afforded alkyl-substituted 2-cyclopentenones. Catalytic hydrogenation of the latter gave the resp. satd. cyclic products as diastereomeric mixts.

URL: http://www.chemie.uni-oldenburg.de/oc/metzger/publikationen/pdf/78.pdf (application/pdf)


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