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
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