Synthesis 2002(9): 1256-1260
DOI: 10.1055/s-2002-32536
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Characterization of Annulene-Fused Pseudorotaxanes

Joshua J. Paka,, Timothy J. R. Weakleya, Michael M. Haley*a, Danny Y. K. Laub, J. Fraser Stoddartb
a Department of Chemistry, University of Oregon, Eugene, OR 97403-1253 USA
Fax: +1(541)3460487; e-Mail: haley@oregon.uoregon.edu;
b Department of Chemistry, University of California - Los Angeles, 405 Hilgard Avenue, Los Angeles, CA 90095 USA
Fax: +1(310)2061843; e-Mail: stoddart@chem.ucla.edu;
Further Information

Publication History

Received 1 April 2002
Publication Date:
28 June 2002 (online)

Abstract

A 24-crown-8 ether-fused dehydrobenzo[18]annulene has been prepared via a stepwise Pd/Cu-mediated strategy. This annulene-crown ether hybrid forms a pseudorotaxane complex in CD2Cl2 with dibenzylammonium hexafluorophosphate when they are combined in a 1:1 ratio, as indicated by 1H NMR spectroscopy and mass spectrometry.

1

Current address: Department of Chemistry, Idaho State University, Pocatello, ID 83209, USA.

16

Crystal data for 2: C48H38O8·C4H8O, M r = 814.93, yellow block, 0.22 × 0.31 × 0.41 mm, monoclinic, space group I2/a, a = 31.788(4), b = 8.6951(13), c = 35.273(4) Å, β = 113.07(1)°, V = 8970(2) Å3, Z = 8, ρcalc = 1.207 g cm-3, MoK α radiation (λ = 0.71073 Å), µ = 0.82 cm-1, F(000) = 3440, T = 23 °C, 2θmax = 23.5°, 13240 independent reflections scanned, 6623 independent reflections in refinement, 550 parameters, R(F) = 0.050 [I σ(I)], wR(F 2 ) = 0.068 (all data). Data were obtained on an Enraf-Nonius CAD-4 Turbo diffractometer. Structure refinement (C, O atoms anisotropic, H atoms riding) was accomplished with teXsan (v. 1.7 for SGI workstations). Crystallographic data (excluding structure factors) for 2 have been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC-182774.