Dibenzotetraaza Crown Ethers: A New Family of Crown Ethers Based on O-Phenyllenediamine

Details

• Personal Author:
  Hausner SH ; Krause-Bauer JA ; Striley CAF ; Zimmer H
• Description:
  Dibenzotetraaza (DBTA) crown ethers possess two o-phenylenediamine moieties. They are homologues of dibenzo crown ether phase-transfer catalysts and were prepared from the condensation of benzimidazoles with oligo(ethyleneglycol) dichlorides and oligo(ethyleneglycol) ditosylates. Compounds with ring sizes ranging from 18-crown-6 to 42-crown-14 were prepared. In addition, various altered benzimidizoles were used to produce DBTA crown ethers with modified substituents and ether bridges, as well as benzimidazolidine crown ethers. The synthetic approach presented here proved to be a convenient route to a new family of crown ethers with overall yields of up to 48% based on the benzimidazole. Yields for the ring-closing step were generally high, ranging from 51% to 94%, without the need for high-dilution conditions. Reaction of the DBTA crown ethers with alkyl and benzyl halides was found to be a facile way to obtain the corresponding tetra(N-organyl) compounds. Picrate extraction studies were carried out to determine phase-transfer catalytic capabilities. Extraction efficiencies for alkali-metal ions were lower than those for dibenzo-18-crown-6. Efficiencies were higher for other metal ions, with some selectivity for Pb(2+). Tetra(N-methyl) DBTA-18-crown-6 generally exhibited higher extraction efficiencies than its N-H analogue, but the selectivity was lower. [Description provided by NIOSH]
• Subjects:
  Chemistry Chemistry, Analytic Ether Occupational Health Safety
• Keywords:
  Analytical-chemistry Analytical-methods Analytical-processes Ethers Organic-chemicals Organic-compounds
• ISSN:
  0022-3263
• Document Type:
  Text
• Genre:
  Journal Article
• Place as Subject:
  Ohio ; OSHA Region 5
• CIO:
  National Institute for Occupational Safety and Health (NIOSH)
• Division:
  DART - Division of Applied Research and Technology
• Topic:
  Workplace Safety & Health
• Location:
  North America
• Volume:
  70
• Issue:
  15
• NIOSHTIC Number:
  nn:20027914
• Citation:
  J Org Chem 2005 Jul; 70(15):5804-5817
• Email:
  shhausner@ucdavis.edu
• CAS Registry Number:
  Lead (CAS RN 7439-92-1)
• Federal Fiscal Year:
  2005
• Peer Reviewed:
  True
• Source Full Name:
  The Journal of Organic Chemistry
• Collection(s):
  National Institute for Occupational Safety and Health
• Main Document Checksum:
  urn:sha-512:a7fc8a4e1378d02b483e7c0f73593143be40e91e2ee236c67da72a052db9ab123463a9ef10929fb3c5e0d0a091f13e5949aa340a72fb152c24282045a00745d4
• Download URL:
  https://stacks.cdc.gov/view/cdc/189670/cdc_189670_DS1.pdf
• File Type:
  [PDF - 242.48 KB ]