The "Photo-Friedel-Crafts Acylation" of 1,4-naphthoquinones

Oelgemoeller, Michael, Schiel, Christian, Fröhlich, Roland, and Mattay, Jochen (2002) The "Photo-Friedel-Crafts Acylation" of 1,4-naphthoquinones. European Journal of Organic Chemistry, 2002 (15). pp. 2465-2474.

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The photochemical reaction between 1,4-naphthoquinone (3) and several aliphatic and aromatic aldehydes 5a−f resulted in the formation of acylated naphthohydroquinones 6a−f in moderate to good yields of 42−79%. When benzaldehyde was used, the dibenzoylated product 7 was also isolated, in 14% yield. The regioselectivity was studied with the unsymmetrical substituted naphthoquinone 4 and butyraldehyde 5b and benzaldehyde 5f. With 5f, the corresponding diaroylated compound 12 was again isolated as a minor product. Oxidation of selected photoproducts afforded the corresponding acylated naphthoquinones 8a, 8b, 8f, and 13 in moderate to excellent yields of 53−94%.

Item ID: 29741
Item Type: Article (Research - C1)
ISSN: 1099-0690
Keywords: acylation; photochemistry; quinones
Date Deposited: 08 Oct 2013 23:43
FoR Codes: 03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030503 Organic Chemical Synthesis @ 40%
03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030504 Organic Green Chemistry @ 30%
03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030505 Physical Organic Chemistry @ 30%
SEO Codes: 97 EXPANDING KNOWLEDGE > 970103 Expanding Knowledge in the Chemical Sciences @ 100%
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