Kinetic Control in the Palladium-Catalyzed Synthesis of C2-Symmetric Hexabenzotriphenylene. A Conformational Study
- 2 May 2000
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (11) , 1629-1632
- https://doi.org/10.1021/ol005916p
Abstract
The hitherto unisolated, thermodynamically unstable C(2)-symmetric conformer of hexabenzotriphenylene (1) has been efficiently synthesized by palladium-catalyzed cyclotrimerization of 9, 10-didehydrophenanthrene (4). The barriers to conformational interconversion of 1 are examined experimentally and by computational studies.Keywords
This publication has 15 references indexed in Scilit:
- Synthesis of Hexabenzotriphenylene and Other Strained Polycyclic Aromatic Hydrocarbons by Palladium-Catalyzed Cyclotrimerization of ArynesOrganic Letters, 1999
- The Structure of Hexabenzotriphenylene and the Problem of Overcrowded “D3h” Polycyclic Aromatic CompoundsJournal of the American Chemical Society, 1999
- An Extraordinarily Twisted Polycyclic Aromatic HydrocarbonAngewandte Chemie International Edition in English, 1997
- Theoretical study of the structures and racemization barriers of [n]helicenes (n = 3–6, 8)Chemical Physics, 1996
- Racemization Barriers of Helicenes: A Computational Study1Journal of the American Chemical Society, 1996
- The Pursuit of PerchlorotriphenyleneThe Journal of Organic Chemistry, 1995
- PerchlorotriphenyleneJournal of the American Chemical Society, 1994
- Empirical model calculations for thermodynamic and structural properties of condensed polycyclic aromatic hydrocarbonsJournal of the American Chemical Society, 1992
- Density-functional exchange-energy approximation with correct asymptotic behaviorPhysical Review A, 1988
- The crystal and molecular structure of dodecafluorotriphenylene, C18F12Journal of Fluorine Chemistry, 1977