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Paper | Special issue | Vol 99, No. 2, 2019, pp.1145-1153
Published online, 28th November, 2018
DOI: 10.3987/COM-18-S(F)85
Synthesis and Properties of a Tricyclic Hexaketone Monohydrate with Hexabutyl Side Chain

Mio Ishita, Masanori Ohkoshi, Yoshiyuki Kuwatani, Hiroyuki Otani, Tohru Nishinaga, and Masahiko Iyoda*

*Department of Chemistry, Graduate School of Science, Tokyo Metropolitan University, Hachioji, Tokyo 192-0397, Japan


A tricyclic hexaketone monohydrate with a hemiacetal structure was synthesized by the ruthenium-catalyzed oxidation of butyl-substituted tribenzotetradehydro[12]annulene-1,2-dione. The oxidation of the annulenedione afforded unique [12]annulene-1,2,5,6,9,10-hexaone, followed by the cyclization to produce corresponding tricyclic hydrate containing two dihydrobenzopyranone rings. The tricyclic hexaketone hydrate weakly interacts with methanol and ethylene glycol to form 1:1 complexes in solution.