title: Synthesis of cyclododeciptycene quinones.
abstract: Cycloiptycenes are elusive and synthetically challenging molecules. We report the first synthesis of two substituted cyclododeciptycene tetraquinones via a sequence of intermolecular and intramolecular Diels-Alder reactions from cis,cis-heptiptycene tetraquinone 2 and substituted 7,16-dihydro-7,16-(o-benzeno)heptacenes 3. Heptiptycene tetraquinone 2 was made from triptycene bisquinone 4 and 1,4-dimethoxyanthracene in three steps, and 6,8,15,17-tetramethoxy-7,16-dihydro-7,16-(o-benzeno)heptacene (3a) was synthesized from triptycene bisquinone 4 and 1,4-dihydro-2,3-benzoxathiin-3-oxide in four steps. The structure of a cyclododeciptycene, 1a, was determined by a single-crystal X-ray analysis. The synthetic sequence is general and should allow the incorporation of various alkoxy and acetoxy substituents appended to the cycloiptycene framework.
authors.affiliation: Department of Chemistry, Kansas State University, Manhattan, Kansas 66506-0401, USA.
authors.forename: Kaiyan
authors.initials: K
authors.lastname: Lou
authors.forename: Allan M
authors.initials: AM
authors.lastname: Prior
authors.forename: Bernard
authors.initials: B
authors.lastname: Wiredu
authors.forename: John
authors.initials: J
authors.lastname: Desper
authors.forename: Duy H
authors.initials: DH
authors.lastname: Hua