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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 30, 2000 - Issue 5
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Original Articles

Synthesis of Hydrophobic Supermacrocyclic Polyethers

, , , &
Pages 849-858 | Received 08 Jun 1999, Published online: 04 Dec 2007

References

  • Pedersen , C. J. 1988 . Angew. Chem. Int. Ed. Engl. , 27 : 1021
  • Cram , D. J. 1988 . Angew. Chem. Int. Ed. Engl. , 27 : 1009
  • Lehn , J.-M. 1988 . Angew. Chem. Int. Ed. Engl. , 27 : 89
  • Weber , E. , Toner , J. L. , Goldberg , I. , Vogtle , F. , Laidler , D. A. , Stoddart , J. F. , Bartsch , R. A. and Liotta , C. L. 1989 . Crown ethers and analogs , Chichester New York Brisbane Toronto Singapore : J. Wiley & Sons .
  • IUPAC nomenclature . 1, 10, 19, 28-tetraoxahexatriacontane for 1, and 1, 11, 21, 31-tetraoxatetracontane for 2.
  • Osawa . have calculated the stable conformation of 1 using MM2 (Osawa, E., Sugiki, T.JSPS 116 Committee Report, 1998, 50, 238.).
  • Kang , S.-K. , Kim , W.-S. and Moon , B.-H. 1985 . Synthesis , : 1161
  • Horita , K. , Yoshioka , T. , Tanaka , T. , Oikawa , Y. and Yonemitsu , O. 1986 . Tetrahedron , 42 : 3021
  • Selected data for 1; m.p. 44.0 – 45.0°C; 1H-NMR (270MHz, δ(CDCl3)) 3.39 (16H, t, J=6.5 Hz), 1.56 (16H, m), 1.32 (32H, bs); 13C-NMR (125MHz, δ (CDCl3)) 70.73 (t), 29.67 (t), 29.26 (t), 26.04 (t); HR-MS (DIP, EI) calcd for C32H64O4 512.4804, found 512.4804.
  • Selected data for 2; m.p. 58.0 – 59.0°C; 1H-NMR (270MHz, δ(CDCl3)) 3.40 (16H, t, J=6.5 Hz), 1.56 (16H, m), 1.32 (40H, bs); 13C-NMR (68MHz, δ (CDCl3)) 70.78 (t), 29.67 (t), 29.44(t), 29.24(t), 26.13(t); HR-MS (DIP, EI) calcd for C36H72O4 568.5430, found 568.5451.
  • McRae , E. G. 1958 . J. Chem. Phys. , 28 : 721
  • Preparation of the supramolecular complex of Ph3C+BF4 − with 1 is currently underway in this laboratory to investigate the characteristics of the molecular train.

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