Nonplanar Aromatic Compounds. 6. [2]Paracyclo[2](2,7)pyrenophane. A Novel Strained Cyclophane and a First Step on the Road to a "Vögtle" Belt

Organic Letters

Volumn 3, Issue 13, 2001, Pages 2093-2096

  Bodwell, Graham J ^a   Miller, David O ^a   Vermeij, Rudolf J ^a  

^a MEMORIAL UNIVERSITY OF NEWFOUNDLAND   (Canada)

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EID: 0000591893     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016053i     Document Type: Article

References (33)

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25. +), 228 (100).
26. 2 with 284 variable parameters led to R1 = 0.059, wR2 = 0.085, GOF = 1.84. CCDC-160393.
27. The angles α and β used here are directly analogous to those used for smaller cyclophanes, such as the [n]paracyclophanes. See ref 17.
28. In determining β angles, the following dummy atoms (Du) were placed in the structure: Du(1) at the C(2)-C(6) centroid: Du(2) at the C(14)-C(16) centroid: Du(3) at the C(21)-C(23) centroid: Du(4) at the C(20)-C(24) centroid.
29. (a) Cyclophanes, Vols. 1 and 2; Keehn, P. M., Rosenfeld, S. M., Eds.; Academic Press: New York, 1983.
30. (b) Vögtle, F. Cyclophan-Chemie; B. G. Teubner: Stuttgart, 1990.
31. (c) Diederich, F. N. Cyclophanes; Royal Society of Chemistry: London, 1991.
32. (d) Hopf, H. Classics in Hydrocarbon Chemistry; Wiley-VCH: Weinheim, 2000.
33. The somewhat large thermal ellipsoids at C(25) and (especially) C(18) mean that the exact values of the measured bond angles and lengths should not be viewed with a high degree of confidence, but there is little doubt that the bond angles are indeed unusually large and the bonds unusually short.