The corresponding author of the paper where this formula was published as appendix passed away. Can someone help me with identifying what is the name of this compound and why have strange zig-zag between Nitrogens

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2 Answers 2


The name of the compound is 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (CAS #: 140681-55-6), which is commonly known as Selectfluor, a trademark of Air Products and Chemicals (see Waylander's comment elsewhere). Different view of the compound is given below (to you to understand the zig-zag feature):


Introduced in 1992, this organic salt is used as a fluorine donor in organic synthesis (Ref.1). For example of using Selectfluor as a source of fluorine, see Ref.2:

Selectfluor as a source of fluorine


  1. R. Eric Banks, Suad N. Mohialdin-Khaffaf, G. Sankar Lal, Iqbal Sharif, Robert G. Syvret, "1-Alkyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts: a novel family of electrophilic fluorinating agents," J. the Chem. Soc., Chem. Commun. 1992, (8), 595-596 (DOI: 10.1039/C39920000595).
  2. Timothy J. Barker, Dale L. Boger, "$\ce{Fe(III)}$/$\ce{NaBH4}$-Mediated Free Radical Hydrofluorination of Unactivated Alkenes," J. Am. Chem. Soc. 2012, 134(33), 13588-13591 (https://doi.org/10.1021/ja3063716).
  • $\begingroup$ is this substance toxic to cells or not environmentally friendly? $\endgroup$
    – SSimon
    Commented Jun 29, 2019 at 13:33
  • $\begingroup$ Not related to the question Which application do you use for these figures? Is there an open-source alternative (if the one you're using is proprietary)? $\endgroup$ Commented Jun 29, 2019 at 15:51
  • 1
    $\begingroup$ @SSimon yes Selectfluor is a toxic substance. PPE is very necessary when handling it. $\endgroup$
    – Waylander
    Commented Jun 29, 2019 at 20:56
  • $\begingroup$ @Waylander thank you. Is there any substance that can give F ions but that is not toxic? $\endgroup$
    – SSimon
    Commented Jun 30, 2019 at 11:36
  • 4
    $\begingroup$ @SSimon - there are many compounds that can give an "F ion" -- i.e., fluoride. For example, NaF gives F ions when dissolved in water. It is sufficiently nontoxic that it is added to toothpaste and drinking water. However, the point of Selectfluor is that is does not donate an ion; it donates a neutral F which forms a covalent bond with the target. Any compound that can perform this function on a wide variety of organic compounds must be toxic. Why? Because people are made out of a wide variety of organic compounds, and we do not want to be fluorinated. $\endgroup$
    – brendan
    Commented Jun 30, 2019 at 21:45

That is generally known as Selectfluor, a source of electrophilic fluorine. The zig-zag line is a 2-D representation of the third ethylene $\ce{-CH2-CH_{2} -}$ unit that links the two nitrogens. more here and wikipedia

  • $\begingroup$ thank you very much. do you know if there is other way to donate F? $\endgroup$
    – SSimon
    Commented Jun 29, 2019 at 7:56
  • 2
    $\begingroup$ Yes, there are several other sources of electrophilic fluorine. This Wikipedia article is a good starting point en.wikipedia.org/wiki/Electrophilic_fluorination $\endgroup$
    – Waylander
    Commented Jun 29, 2019 at 8:24

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