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
<A NAME="RS19306ST-1">1</A>
Scott LT.
Hashemi MM.
Meyer DT.
Warren HB.
J. Am. Chem. Soc.
1991,
113:
7082
<A NAME="RS19306ST-2">2</A>
Stoddart MW.
Brownie JH.
Baird MC.
Schmider HL.
J. Organomet. Chem.
2005,
690:
3440
<A NAME="RS19306ST-3">3</A>
Sakurai H.
Daiko T.
Sakane H.
Amaya T.
Hirao T.
J. Am. Chem. Soc.
2005,
127:
11580
<A NAME="RS19306ST-4">4</A>
Dyker G.
J. Org. Chem.
1993,
58:
234
<A NAME="RS19306ST-5">5</A>
Waldvogel SR.
Mirk D. In
Handbook of C-H Transformations
Wiley-VCH;
Weinheim:
2005.
p.251-261
<A NAME="RS19306ST-6">6</A>
Dyker G.
Heiermann J.
Miura M.
Pivsa-Art S.
Satoh T.
Nomura M.
Chem. Eur. J.
2000,
6:
3426
<A NAME="RS19306ST-7">7</A>
Dyker G.
Chem. Ber./Recl.
1997,
130:
1567
<A NAME="RS19306ST-8">8</A>
Gundermann KD.
Z. Naturforsch., B: Chem. Sci.
1992,
47:
1764
<A NAME="RS19306ST-9">9</A>
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].
<A NAME="RS19306ST-10">10</A>
Muth E.
Ph.D. Thesis
Bochum University;
Germany:
2004.
<A NAME="RS19306ST-11">11</A>
Catellani M.
Motti E.
New J. Chem.
1998,
22:
759
<A NAME="RS19306ST-12">12</A>
Alder RW.
Colclough D.
Grams F.
Orpen AG.
Tetrahedron
1990,
46:
7933
<A NAME="RS19306ST-13">13</A>
Olah GA.
Husain A.
Gupta BGB.
Narang SC.
Angew. Chem.
1981,
93:
705
<A NAME="RS19306ST-14">14</A>
Simpson CD.
Brand JD.
Berresheim AJ.
Przybilla L.
Räder HJ.
Müllen K.
Chem. Eur. J.
2002,
8:
1424
<A NAME="RS19306ST-15">15</A>
Klumpp DA.
Baek DN.
Prakash GKS.
Olah GA.
J. Org. Chem.
1997,
62:
6666
