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Synthesis of the first perfluoro-spiro-bis-crown ethers

Journal Article · · Journal of Organic Chemistry
DOI:https://doi.org/10.1021/jo961628o· OSTI ID:543166
; ;  [1]
  1. Univ. of Texas, Austin, TX (United States)

Since the first perfluoro crown ethers were prepared by members of our research group, many new perfluoro crown ethers have been synthesized, and medical applications such as {sup 19}F NMR imaging and oxygen carrier applications as well as new chemistry associated with these compounds are currently under study. Perfluoro crown ethers do not form extremely stable complexes with metal cations because the basicities of perfluoro crown ethers decrease as the amount of fluorine substitution increases. On the contrary, perfluoro crown ethers form complexes with certain anions in the gas phase. In order to explore the chemistry of theses new compounds, the preparation of new perfluoro crown ethers, such as multilooped perfluoro crown ethers, is very important. We report in this paper the syntheses of the first perfluoro-spiro-bis[19]crown ethers, perfluoro-spiro-bis-crown-6 (1), perfluoro-spiro-bis[16]crown-5 (2), and perfluoro-spiro-bis[13]crown-4 (3), by elemental fluorine. 12 refs., 3 figs., 1 tab.

DOE Contract Number:
FG05-91ER12119
OSTI ID:
543166
Journal Information:
Journal of Organic Chemistry, Journal Name: Journal of Organic Chemistry Journal Issue: 5 Vol. 62; ISSN 0022-3263; ISSN JOCEAH
Country of Publication:
United States
Language:
English

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