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Alkylaluminium Dichloride Induced Friedel-Crafts Acylation of Unsaturated Carboxylic Acids and Alcohols (1993)

Metzger, Jürgen O. ; Biermann, Ursula

Weinheim : Wiley-Blackwell

Liebigs Annalen 1993 (1993), S. 645-650

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ISSN: 0170-2041

Keywords: Friedel-Crafts acylation ; β,γ-Unsaturated keto carboxylic acids and alcohols ; Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: The ethylaluminium dichloride induced Friedel-Crafts acylation of unsaturated carboxylic acids, for example 10-undecenoic acid (1a) and oleic acid (5a), and of the respective alcohols 1b and 5b with acyl chlorides and cyclic acyl anhydrides gave the corresponding long-chain β,γ-unsaturated ketones 3, 6/7, 11 and 13/14 with ω-carboxy and ω-hydroxy functions, respectively. The intramolecular cyclization of petroselinic acid chloride (17) yielded (E)-2-dodecylidenecyclohexanone (18). Catalytic hydrogenation gave the respective saturated ketones 4, 8/9, 12, 15/16 and 19.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/jlac.1993199301105

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