title: Design and synthesis of the first triply twisted Möbius annulene.
abstract: As long as 50 years ago theoretical calculations predicted that Möbius annulenes with only one π surface and one edge would exhibit peculiar electronic properties and violate the Hückel rules. Numerous synthetic attempts notwithstanding, the first singly twisted Möbius annulene was not prepared until 2003. Here we present a general, rational strategy to synthesize triply or even more highly twisted cyclic π systems. We apply this strategy to the preparation of a triply twisted [24]dehydroannulene, the structure of which was confirmed by X-ray analysis. Our strategy is based on the topological transformation of 'twist' into 'writhe'. The advantage is twofold: the product exhibits a lower degree of strain and precursors can be designed that inherently include the writhe, which, after cyclization, ends up in the Möbius product. With our strategy, triply twisted systems are easier to prepare than their singly twisted counterparts.
authors.affiliation: Institute for Organic Chemistry, University of Kiel, Otto-Hahn Platz 4, 24098 Kiel, Germany.
authors.forename: Gaston R
authors.initials: GR
authors.lastname: Schaller
authors.affiliation: Department of Chemistry, Nanoscience Center, University of Jyväskylä, PO Box 35, 40014 Jyväskylä, Finland.
authors.forename: Filip
authors.initials: F
authors.lastname: Topić
authors.affiliation: Department of Chemistry, Nanoscience Center, University of Jyväskylä, PO Box 35, 40014 Jyväskylä, Finland.
authors.forename: Kari
authors.identifier: 0000000272828419
authors.initials: K
authors.lastname: Rissanen
authors.affiliation: Nagoya University, 1E Miyahigashi-cho, Showa-ku, Nagoya 466-0804, Japan.
authors.forename: Yoshio
authors.initials: Y
authors.lastname: Okamoto
authors.affiliation: College of Materials Science and Chemical Engineering, Harbin Engineering University, 145 Nantong Street, Harbin 150001, China.
authors.forename: Jun
authors.initials: J
authors.lastname: Shen
authors.affiliation: Institute for Organic Chemistry, University of Kiel, Otto-Hahn Platz 4, 24098 Kiel, Germany.
authors.forename: Rainer
authors.initials: R
authors.lastname: Herges
mesh_terms: D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure
chemical_list: D047028:Macrocyclic Compounds