Efficient fragment coupling approaches toward large oxacalix[n]arenes (n = 6, 8)

Organic Letters

Volumn 11, Issue 8, 2009, Pages 1681-1684

  Van Rossom, Wim ^a   Ovaere, Margriet ^a,b   Van Meervelt, Luc ^a,b   Dehaen, Wim ^a   Maes, Wouter ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

^b Department of Chemistry ^*  (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 65249145651     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900116h     Document Type: Article

References (37)

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26. 6f
27. 6b They demonstrated that functionalized oxacalix[8]arenes are accessible by removal of the resorcinarene template from their cavitand structures.
28. A considerable part of the excess of (res)orcinol (-75%) can be recovered on chromatographic purification.
29. 6h
30. 6h
31. Too strong dilution has to be avoided; no (or very slow) reaction has been observed under such conditions.
32. NAr functionalization in DMF at 90 °C (the conditions optimized for the oxacalix[4]arene) and the reduced yield seem to reflect the lower stability of larger oxacalix[n]arenes.
33. For the opposite combination, the conditions (DMF, 90 °C) required to prepare the pentaaryl are likely to induce scrambling.
34. Full synthetic details for this compound can be found in ref 6h.
35. Crystallographic data (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Centre as suppl. publ. no. CCDC-718550. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
36. Katz reported the structure of an oxacalix[6]- and an oxacalix[8]arene at the Calix 2007 conference (College Park, MD).
37. 6]oxacyclophanes were very recently reported: Ma. M.; Wang, H.: Li, X.; Liu. L.; Jin. H.; Wen, K. Tetrahedron 2009, 65, 300.