Chiral 1,10-phenanthroline-bridged calix[6]arenes

European Journal of Organic Chemistry

Volumn , Issue 20, 2006, Pages 4717-4730

  Konrad, Serge ^a   Bolte, Michael ^b   Näther, Christian ^a   Lüning, Ulrich ^a  

^a UNIVERSITY OF KIEL   (Germany)

^b GOETHE UNIVERSITY   (Germany)

Author keywords

C2 chirality; Calixarenes; Heterocycles; Macrocycles; Supramolecular chemistry

Indexed keywords

EID: 33750398740     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600295     Document Type: Article

References (46)

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22. [20]; u = up, d = down, i = in. In bridged compounds, the description of the orientation of each arene ring begins at a bridgehead (ring A per definition). Thus, the other bridgehead is labeled D. If a remaining phenol group is substituted, this ring is labeled B, thus defining the labeling of all other rings. In the non-bridged calixarenes, a functionalized phenol ring defines ring A. The descriptors up and down are used as follows: in bridged calixarenes, the side of the bridge is labeled up, in non-bridged derivatives, ring A is up by definition.
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31. 21x denominates one enriched (90%) diastereoisomer of the 21a/21b mixture. An assignment was not possible.
32. H. Fritschi, U. Leutenegger, A. Pfaltz, Helv. Chim. Acta 1988, 71, 1553-1565.
33. H. C. Brown, G. Zweifel, J. Am. Chem. Soc. 1961, 83, 2544-2551. The reaction time for the formation of the trialkylborane was increased to 15 h.
34. * = The assignments may be interchanged.
35. * = The assignments are uncertain, # = assignments may be interchanged. Signals for C atoms 1, 3, 13, 19, 21 und 31 could not be found, they are probably superimposed by other signals.
36. Protons carrying the same letter are bound to the same aromatic ring or are part of the same methylene group. tert-Butyl groups with the same index give rise to one signal at higher temperature (60°C).
37. The assignment does not differentiate between the methylene groups between the aryl rings and the methylene groups next to an ether oxygen atom (x = O, Ar).
38. Not all signals could be identified and assigned.
39. The aromatic signals are interpreted as doublets although being part of a AA'MM' system.
40. After evaporating excess solvent for days at <0.1 mbar, still solvent can be found by NMR and elemental analysis.
41. Not all signals could be identified and assigned. The signals of the myrtanyl subunit were assigned in analogy to 13.
42. 2 groups carry the letters a-f. These letters do not correspond to the labeling of the phenol rings A-F.
43. 13C NMR spectrum.
44. The yield is corrected to the purity of 90%.
45. 2 groups.
46. M. Hagen, U. Lüning, Chem. Ber.lRecueil 1997, 130, 231-234.