title: Dodecamethoxy- and hexaoxotricyclobutabenzene: synthesis and characterization.
abstract: We report herein the syntheses of dodecamethoxytricyclobutabenzene (TCBB) 1 and hexaoxo-TCBB 2, a class of molecules with structural and theoretical interest. The preparation is based on the 3-fold [2 + 2] cycloadditions of benzyne and ketene silyl acetals (KSAs), where the selectively protected 2-iodophloroglucinol derivative served as a synthetic equivalent of benztriyne I, allowing rapid and regioselective annulation of fully functionalized four-membered rings. Structural study on the former compound showed that the C-C bond lengths in the central benzene ring were essentially the same.
authors.affiliation: Interactive Research Center of Science, Department of Chemistry, Tokyo Institute of Technology, SORST, Japan Science and Technology Corporation (JST), O-okayama, Meguro-ku, Tokyo 152-8551, Japan.
authors.forename: Toshiyuki
authors.initials: T
authors.lastname: Hamura
authors.forename: Yousuke
authors.initials: Y
authors.lastname: Ibusuki
authors.forename: Hidehiro
authors.initials: H
authors.lastname: Uekusa
authors.forename: Takashi
authors.initials: T
authors.lastname: Matsumoto
authors.forename: Jay S
authors.initials: JS
authors.lastname: Siegel
authors.forename: Kim K
authors.initials: KK
authors.lastname: Baldridge
authors.forename: Keisuke
authors.initials: K
authors.lastname: Suzuki