The solarchemical Photo-Friedel Crafts acylation of quinones

Oelgemoeller, Michael, Schiel, Christian, Ortner, Jürgen, and Mattay, Jochen (2002) The solarchemical Photo-Friedel Crafts acylation of quinones. In: UNSPECIFIED, (ed.) AG Solar Nordrhein-Westfalen: Solare Chemie und Materialforschung, Förderzeitraum 1995-2001. AG-Solar Nordrhen Westfalen, Köln, pp. 1-13.

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Photochemical reactions between 1,4-quinones and several aliphatic or aromatic aldehydes were investigated under artificial and solar irradiation conditions. These reactions selectively gave the corresponding acylated hydroquinones in moderate to good yields. Dibenzoylated products arising from secondary acylation were isolated in minor amounts only when benz- or acetaldehyde was used as starting material. The regioselectivity of the acylation was studied with unsymmetrical substituted juglone derivatives, and could be totally controlled in favour of the 2.5-regioisomer by saturation with LiClO₄. Three different solar reactors (PROPHIS, CPC, and flat-bed reactor) were used for the photochemical syntheses with sunlight, and the CPC system was found to be the most robust one in terms of weather dependence. The latter reactions were easily performed on a half-kilogram scale using cheap and commercially available starting materials, and yielding important key-intermediates for pharmaceuticals.

Item ID: 29980
Item Type: Book Chapter (Non-Commercial)
ISBN: 978-3-89336-306-3
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Published on CD-ROM.

Date Deposited: 17 Jul 2014 00:34
FoR Codes: 03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030503 Organic Chemical Synthesis @ 40%
03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030504 Organic Green Chemistry @ 60%
SEO Codes: 97 EXPANDING KNOWLEDGE > 970103 Expanding Knowledge in the Chemical Sciences @ 100%
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