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Communication | Special issue | Vol 62, No. 1, 2004, pp.153-159
Published online, 4th November, 2003
DOI: 10.3987/COM-03-S(P)24
Endoperoxidation of 9,10-Bis(1-hydroxyalkyl)anthracenes and Successive Formation of 9,10-Anthraquinone under Grignard Reaction Conditions

Shigeyasu Kuroda,* Mitsunori Oda,* Hiroki Syumiya, Shah M. I. Shaheen, Ryuta Miyatake, Teruhiko Nishikawa, Akiko Yoneda, Tokiko Tanaka, Masaru Mouri, and Mayumi Kyogoku

*Department of Applied Chemistry, Faculty of Engineering, Toyama University, Gofuku 3190, Toyama 930-8555, Japan

Abstract

The reaction of anthracene-9,10-carboaldehyde with various Grignard reagents under ambient conditions gave 9,10-bis(1-hydroxyalkyl)anthracene-9,10-peroxides and 9,10-anthraquinone as the first example. The endoperoxidation of 9,10-bis(1-hydroxyalkyl)anthracenes was assisted by the lone paired electron of oxygen in the side chain, and the endoperoxides were transformed to anthraquinone by the Grignard reagents.