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Volumn 11, Issue 3, 2009, Pages 673-676

Synthesis of the first calix[6]crypturea via a versatile tris-azide precursor

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Indexed keywords


EID: 62149124687     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8027384     Document Type: Article
Times cited : (45)

References (42)
  • 1
    • 0004287470 scopus 로고    scopus 로고
    • Asfari, Z, Böhmer, V, Harrowfield, J, Vicens, J, Eds, Kluwer Academic Publishers: Dordrecht, The Netherlands
    • (a) Asfari, Z., Böhmer, V., Harrowfield, J., Vicens, J., Eds.; Calixarenes 2001; Kluwer Academic Publishers: Dordrecht, The Netherlands, 2001.
    • (2001) Calixarenes 2001
  • 2
    • 0004266535 scopus 로고    scopus 로고
    • Mandolini, L, Ungaro, R, Eds, Imperial College Press: London
    • (b) Mandolini, L., Ungaro, R., Eds.; Calixarenes in Action; Imperial College Press: London, 2000.
    • (2000) Calixarenes in Action
  • 30
    • 0030738741 scopus 로고    scopus 로고
    • However, polyazido intermediates have been already involved in [1 + 1] macrocyclization reactions, leading either to tris-imine, tris-phosphazide, or tris-triazole derivatives; see, respectively: ref 9. Alajari'n, M.; Molina, P.; López-Lázaro, A.; Foces-Foces, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 67-70.
    • However, polyazido intermediates have been already involved in [1 + 1] macrocyclization reactions, leading either to tris-imine, tris-phosphazide, or tris-triazole derivatives; see, respectively: ref 9. Alajari'n, M.; Molina, P.; López-Lázaro, A.; Foces-Foces, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 67-70.
  • 32
    • 57549098217 scopus 로고    scopus 로고
    • For macrocyclization reactions between polyamines and calix[4]arenes, see:Hamdi, A.; Lee, Y. H.; Kim, Y.; Kusumahastuti, D. K. A.; Ohio, K.; Abidi, R.; Vicens, J. Tetrahedron Lett. 2009, 50, 540-543, and references therein.
    • For macrocyclization reactions between polyamines and calix[4]arenes, see:Hamdi, A.; Lee, Y. H.; Kim, Y.; Kusumahastuti, D. K. A.; Ohio, K.; Abidi, R.; Vicens, J. Tetrahedron Lett. 2009, 50, 540-543, and references therein.
  • 37
    • 62149088985 scopus 로고    scopus 로고
    • 1H NMR spectrum of the crude material.
    • 1H NMR spectrum of the crude material.
  • 38
    • 0010406433 scopus 로고    scopus 로고
    • 3 bearing bulky groups. See:van Duynhoven, J. P. M.; Janssen, R. G.; Verboom, W.; Franken, S. M.; Casnati, A.; Pochini, A.; Ungaro, R.; de Mendoza, J.; Nieto, P. M.; Prados, P.; Reinhoudt, D. N. J. Am. Chem. Soc. 1994, 116, 5814-5822.
    • 3 bearing bulky groups. See:van Duynhoven, J. P. M.; Janssen, R. G.; Verboom, W.; Franken, S. M.; Casnati, A.; Pochini, A.; Ungaro, R.; de Mendoza, J.; Nieto, P. M.; Prados, P.; Reinhoudt, D. N. J. Am. Chem. Soc. 1994, 116, 5814-5822.
  • 39
    • 62149149993 scopus 로고    scopus 로고
    • Similar conformational properties were observed for 5. See ref 3
    • Similar conformational properties were observed for 5. See ref 3.
  • 40
    • 62149115735 scopus 로고    scopus 로고
    • See Supporting Information
    • See Supporting Information.
  • 41
    • 62149111552 scopus 로고    scopus 로고
    • The complexation process is fast on the NMR time scale
    • The complexation process is fast on the NMR time scale.
  • 42
    • 62149120690 scopus 로고    scopus 로고
    • 1H VTNMR study of this mixture of complexes was undertaken between 258 and 328 K (see Supporting Information).
    • 1H VTNMR study of this mixture of complexes was undertaken between 258 and 328 K (see Supporting Information).


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