Abstract
A bisnaphthyl-substituted acenaphthylene is synthesized via two independent two-step procedures, Pd-catalyzed and classically with Grignard reagents. The subsequent dehydrocyclization stops after the first carbon-carbon bond formation, leading to an octacyclic π-system as the main product.
Key words
palladium - Heck reaction - polycyclic aromatic - hydrocarbons - annulated cyclopentadienes
References and Notes
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9 X-ray data for 5 were collected on a Bruker AXS-SMART 1000 (Mo Kα radiation). The structure was solved by direct methods and refined by full matrix least squares using SHELXTL-97 All non-hydrogen atoms were refined using anisotropic thermal parameters.
Crystal Data for 5
T = 213(2) K, C32H20, M = 404.48, monoclinic space group P21/n, a = 12.190(5) Å, b = 10.104(4) Å, c = 17.237(7) Å, β = 102.484(9)°, V = 2072.9(15) Å3, Z = 4, D
C = 1.296 g/cm3, µ = 0.073 mm-1, 2.35° < Θ < 25.15°, reflections collected/unique 10788/3646 [R
int = 0.0489], data/restraints/parameters 3646/0/289, GOF 1.021, final R[I > 2σ(I)] R1 = 0.0416, wR2 (all data) = 0.1082, residual density 0.134 and -0.190 e A-3.
Crystal Data for 6
The crystals were of poor quality, twinned and weakly diffracting. C32H20, M = 404.48, monoclinic space group P21/c, a = 11.352(3) Å, b = 24.248(4) Å, c = 7.835(2) Å, β = 96.80(2)°, V = 2141.4(8) Å3, Z = 4, T = 293(2) K, µ = 0.071 mm-1, 32624/3877/2025 reflections collected/unique/observed, R
int = 0.1775, R1 = 0.1268, wR2 (all data) = 0.2319, 290 parameters. All non-hydrogen atoms calculated anisotropic; positions of the H atoms calculated for idealized positions. The structure was solved and refined using SHELXTL-97 (G. M. Sheldrick, Universität Göttingen 1997).
Crystal Data for 11
Again, the crystals were of poor quality and weakly diffracting. C32H20, M = 404.48, tetragonal space group I-4, a = 20.673(2) Å, c = 10.448(1) Å, V = 4465.4(9) Å3, Z = 8, T = 293(2) K, µ = 0.068 mm-1, 2380/1798/934 reflections collected/unique/observed, R
int = 0.0670, R1 = 0.1283, wR2 (all data) = 0.3307, 289 parameters. All non-hydrogen atoms calculated anisotropic; positions of the H atoms calculated for idealized positions. The structure was solved and refined using SHELXTL-97 (G. M. Sheldrick, Universität Göttingen 1997).
X-ray data have been deposited at the Cambridge Crystallographic Data Centre (deposition numbers CCDC-611565 for 5, CCDC-614432 for 6 and CCDC-614433 for 11. Copies of the data can be obtained free of charge at www.ccdc.cam.uk/data_request/cif or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ [fax: +44 (1223)336033; e-mail: deposit@ccdc.cam.ac.uk].
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