Advertisement

Synthesis of new bis-diphenyl-22-and diphenyl-11-membered ring N-pivot lariat crown ethers

  • Niu Changrong
  • Luo Tiejun
  • Wu Chengtai
  • He Yongbin
Article

Abstract

Bis-diphenyl 22 and 11-Membered Ring N-pivot lariat Crown Ethers[1,2] were prepared by one step reaction of 2,2′-dihydroxy-diphenyl with N-tosyl-diethanolamine ditoskylate in DMF at refluxing temperature under N2, Using anhydrous potassium carbonate as condensing agent, respectirely. The tosyl group of (1,2) were removed by treatment with 40% HBr in AcoH in the presence gf a large amount of phenol to give correspondence crown ether compounds (3,4). New N-pirot lariat crown thers (5,6) were prepared by one step reaction of (3) with RBr (R=−CH2CH=CH2, −CH2(CH2)14CH3) in CH3CN at, refluxing temperature under N2, Using anhydrous K2CO3 as condensing, agent. New N-pivot lariat croon ether(7) were prepared by one step reaction (4) withn-bromohexadecane in CH3CN at refluxing temperature under N2, Using anhydrous potassium carbonate as condensing agent. New compounds (1,3,5,6,7) were characterized by IR,1H NMR, Ms and elemental analysis.

Key words

2,2′-dihydroxydiphenyl Diphenyl-N-pivot lariat crown ether Synthesis 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Dishong D M, Diamond C J, Cinoman M J,et al. Crown cation complex effects 20: Syntheses and cation binding properties of carbon-pivot lariat ethers.J Am Chem Soc 1983,105: 586CrossRefGoogle Scholar
  2. 2.
    Ikeda I, Emmura H, Okahara M. Hydrophilicity and complexing ability of alkyl lariat ethers.Bull Chem Sol Jpn, 1984,57: 1612–1616CrossRefGoogle Scholar
  3. 3.
    Hosseini M W, Lehn J M, Steven R,et al. Synthesis of mono-and difunctionalized ditopic (24) N6O2 macrocyclic receptor molecules.J Org Chem, 1987,52: 1662–1666CrossRefGoogle Scholar
  4. 4.
    Lehn J M. Supromolecular chemistry: Receptors, catalysts, and carriers.Science (washington D. C), 1985,227: 849–856CrossRefGoogle Scholar
  5. 5.
    Yohannes P G, Mertes M P, Mertes K B. Pyrophosphate formation via a phosphoramidate intermediate in polyammonium macrocycle/metal ion-Catalyzed Hydrolysis or ATP.J Am Chem Soc 1985,107: 8288–8289CrossRefGoogle Scholar
  6. 6.
    Pietraszkiewicz M, Jurczak J. Synthesis of novel chiral macrocyclic lagands bearing methyl 4,6-O-benzylidene-α-d-mannopyranoside.J Chem Soc Chem Commum, 1983, 132–133Google Scholar
  7. 7.
    Bradshaw T S, Krakowiak K E, Haoyun An,et al. The synthesis of new diaza/IN-pivot lariat 15-crown-5 and 18-crown-6 macrocycles.Tetrahe-dron, 1990,46: 1163–1170CrossRefGoogle Scholar
  8. 8.
    Liu G, Niu C R, Wu C T. Studies on synthesis of New biphenyl 11, 14 and 17-membered ring N-pivot lariat crown ethers.Youji Huaxue, 1996,16: 23–28 (in Chinese)Google Scholar

Copyright information

© Springer 1997

Authors and Affiliations

  • Niu Changrong
    • 1
  • Luo Tiejun
    • 1
  • Wu Chengtai
    • 1
  • He Yongbin
    • 1
  1. 1.Department of ChemistryWuhan UniversityWuhanChina

Personalised recommendations