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Synthesis 2001(8): 1275-1279
DOI: 10.1055/s-2001-15072
PAPER
© Georg Thieme Verlag Stuttgart · New York

Photoacylation of Electron-Rich Quinones: An Application of the ”Photo-Friedel-Crafts Reaction”

Christian Schiela, Michael Oelgemöllerb, Jochen Mattay*,a
a Organische Chemie I, Fakultät Chemie, Universität Bielefeld, Postfach 10 01 31, 33501 Bielefeld, Germany
Fax: +49(521)1066427; e-Mail: mattay@uni-bielefeld.de;
b Present address: Inoue Photochirogenesis Project, ERATO, JST, 4-6-3 Kamishinden, Toyonaka-shi, Osaka, 560-0085, Japan
Further Information

Publication History

Received 13 March 2001
Publication Date:
24 September 2004 (online)

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Abstract

Irradiation of substituted 1,4-benzo- or 1,4-naphthoquinones in the presence of several aldehydes resulted in the formation of acylated hydroquinones in good yields. In the case of 5-acetyloxy naphthoquinone 8, both regioisomers were formed, but the 2,8-isomer was favored in all cases examined. Even acylated tetrahydroxy naphthalenes became available in good yields by this method.

Key words

acylation - quinones - photochemistry

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The results from the solarchemical experiments will be published independently.