Journal ArticleDOI
Multifaceted consequences of holding two [8]annulene rings face-to-face. Synthesis, structural characteristics, and reduction behavior of [22](1,5)cyclooctatetraenophane
Leo A. Paquette,Mark A. Kesselmayer,Gail E. Underiner,Stephen D. House,Robin D. Rogers,Klaus Meerholz,Jürgen Heinze +6 more
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The doubly-decked semibulled annulene 11 has been prepared in 13 steps from octahydro 3a,9a-propenocyclopentacycloocten-2,11-dione as mentioned in this paper.Abstract:
The doubly-decked [8]annulene 11 has been prepared in 13 steps from octahydro 3a,9a-propenocyclopentacycloocten-2,11-dione. The scheme takes advantage of the annulating capacity of the Cook-Weiss reaction and the ability of semibullvalenes to undergo thermal isomerization to cyclooctatetraenes. Bis(semibullvalene) is both conformationally dynamic and subject to very rapid Cope rearrangement. The energetics of inversion within its interconnective cyclooctane ring have been elucidated by variable-temperature 1 H NMR spectroscopyread more
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Journal ArticleDOI
Renaissance of annulene chemistry.
Journal ArticleDOI
Three-dimensional aromaticity in an antiaromatic cyclophane.
Ryo Nozawa,Jin Seok Kim,Juwon Oh,Anna Lamping,Yemei Wang,Soji Shimizu,Ichiro Hisaki,Tim Kowalczyk,Heike Fliegl,Dongho Kim,Hiroshi Shinokubo +10 more
TL;DR: A cyclophane is synthesised, in which two antiaromatic porphyrin moieties adopt a stacked face-to-face geometry with a distance shorter than the sum of the van der Waals radii of the atoms involved, which corroborates the existence of attractive interactions between twoAntiaromatic π-systems.
Journal ArticleDOI
The Effects of Substituents on the Degenerate Cope Rearrangement of Semibullvalenes and Barbaralanes
TL;DR: In this article, the activation parameters for degenerate Cope rearrangements of barbaralane and several semibullvalenes were determined by variable-temperature carbon-13 NMR spectroscopy at 126 and 151 MHz.
Book ChapterDOI
Transition metal complexes of (strained) cyclophanes
Jürgen Schulz,Fritz Vögtle +1 more
TL;DR: In this article, a tricarbonylchromium complex of a chiral [2.2]metacyclophane was determined by X-ray crystallography and its absolute configuration, containing two elements of chirality, was determined.
Journal ArticleDOI
Darstellung, Struktur und konformatives Verhalten gespannter Adamantanophane
TL;DR: In this article, the araliphanes 3(a), 5-7a, 10-a, and 11 are synthesized and the crystal structure of 15 is described.