Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2007 Jun;128(6):674-678.
doi: 10.1016/j.jfluchem.2007.03.012.

Photochemical Schiemann Reaction in Ionic Liquids

Jorge Heredia-Moya  1 , Kenneth L Kirk
Affiliations

Photochemical Schiemann Reaction in Ionic Liquids

Jorge Heredia-Moya et al. J Fluor Chem. 2007 Jun.

Abstract

Photochemical Schiemann reactions of imidazole derivatives 1 and 4 were carried out in 1-butyl-3-methylimidazolium tetrafluoroborate ionic liquid [bmim][BF(4)] as solvent. The effects of temperature, co-solvent and wavelength on the rate of the reaction and product yield were examined. The use of ionic liquid increases the yield of the photochemical fluorodediazoniation reaction of 2 at 0°C. Careful temperature control is necessary to minimize the photodecomposition of the ionic liquid in order to increase the yield of product.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Absorbance of [bmim][BF4]. (a) before and (b) after irradiation.
Scheme 1
Scheme 1
One-pot diazotization-photochemical fluorodediazoniation in [bmim][BF4]
Scheme 2
Scheme 2
Diazotization-photochemical fluorodediazoniation reaction of 4 in [bmim][BF4]
See this image and copyright information in PMC

References

    1. Balz G, Schiemann G. Chem Ber. 1927;60:1186.
    1. Kirk KL, Cohen LA. J Am Chem Soc. 1971;93:3060–3061. - PubMed
    2. Kirk KL, Cohen LA. J Am Chem Soc. 1973;95:4619–4624. - PubMed
    3. Kirk KL, Nagai W, Cohen LA. J Am Chem Soc. 1973;95:8389–8392. - PubMed
    1. Langlois B. In: Methods of Organic Chemistry (Houben-Weyl). Organo-Fluorine Compounds. Basner B, Hagemann H, Tatlow JC, editors. 10a. Thieme; Stuttgart: 2000. pp. 686–740.
    1. Kirk KL, Cohen LA. In: Biochemistry of the Carbon-Fluorine Bond, ACS Symposium Series. Filler R, editor. 1976. pp. 23–36.
    1. Milanesi A, Farnoni M, Albini A. J Org Chem. 2005;70:603–610. - PubMed
    2. Canning PSJ, McCrudden K, Maskill H, Sexton B. J Chem Soc Perkin Trans. 1999;2:2735–2740.

LinkOut - more resources