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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 19, 1989 - Issue 5-6
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Original Articles

Fifty-Two Membered Macromonocyclic Polyamine Possessing Twelve Nitrogen Atoms in the Ring: Cyclic Spermine Tetramer

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Pages 1009-1014 | Received 28 Sep 1988, Published online: 24 Oct 2006

References

  • Ganem , B. 1982 . Acc. Chem. Res. , 15 : 290
  • Tabor , C. W. and Tabor , H. 1984 . Ann. Rev. Biochem. , 53 : 749
  • Potvin , P. G. and Lehn , J.-M. 1987 . Progress in Macrocyclic Chemistry Vol. 3. Synthesis of Macrocycles , Edited by: Izatt , R. M. and Christensen , J. J. 167 – 239 . New York : John Wiley and Sons .
  • Iwata , M. and Kuzuhara , H. 1986 . Chem. Lett. , : 951
  • Hosseini , M. W. and Lehn , J.-M. 1986 . Helv. Chim. Acta. , 69 : 587
  • For accommodation of three methylene blocks, 2 and 3 were employed, without intention. 4 was employed for accommodation of four methylene chains.
  • Vriesema , B. K. , Buter , J. and Kellogg , R. M. 1984 . J. Org. Chem. , 49 : 110
  • 1,5,9,14,18,22,27,31,35,40,44,48-dodecatosyl-1,5,9,14,18,22,27,31,35,40,44,48-dodecaazacyclodopentacontane (1): Calcd for C124H164O24N12S12 (2591.44) : C, 57.47; H, 6.34; N, 6.49; S, 14.85%. Found: C, 57.18; H, 6.49; N, 6.20; S, 14.63%. IR (KBr) v 1330 and 1155 (SO2) cm −1. 1H-NMR (CDCl3), δ 1.50 (4 parts, FIN-protons9)), 1.81 (4, TIN-Protons9)), 2.39 (9, ArMe-protons9)), 3.06 (4, FOU-protons9)), 3.06 (8, TOU-protons9)), 7.27 (6, ArHme-protons9)), and 7.62 and 7.63 (6, ArHs-protons7)).
  • FIN-protons designate the internal two methylene protons of contiguous four methylene chains sectioned by nitrogen atom such as -N-CH2-CH 2-CH 2-CH2-N-. TIN-Protons designate the central methylene protons of contiguous three methylene chains sectioned by nitrogen atom such as -N-CH2-CH 2-CH2-N-. FOU-protons designate the external two methylene protons of contiguous four methylene chains sectioned by nitrogen atom such as -N-CH 2-CH2-CH2-CH 2-N-. TOU-protons designate the external two methylene protons of contiguous three methylene chains sectioned by nitrogen atom such as -N-CH 2-CH2-CH 2-N-. ArMe-protons designate methyl protons attached to aromatic ring. ArHme-protons designate aromatic protons disposed at position ortho to the methyl group. ArHs-protons designate aromatic protons disposed at position ortho to the sulfonyl group.

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