Selectfluor

Selectfluor

100px 100px
Names
IUPAC names 1-(chloromethyl)-4-fluoro-1,4-diazo niabicyclo[2.2.2]octane ditetrafluoroborate
Other names F-TEDA, N-Chloromethyl-N-fluorotriethylenediammonium bis(tetrafluoroborate)
Identifiers
CAS Number	140681-55-6 Y
ChemSpider	2007047 N
EC Number	414-380-4
Jmol 3D model	Interactive image
PubChem	2724933
InChI InChI=1S/C7H14ClFN2.2BF4/c8-7-10-1-4-11(9,5-2-10)6-3-10;2*2-1(3,4)5/h1-7H2;;/q+2;2*-1 N Key: TXRPHPUGYLSHCX-UHFFFAOYSA-N N InChI=1/C7H14ClFN2.2BF4/c8-7-10-1-4-11(9,5-2-10)6-3-10;2*2-1(3,4)5/h1-7H2;;/q+2;2*-1 Key: TXRPHPUGYLSHCX-UHFFFAOYAI
SMILES [B-](F)(F)(F)F.[B-](F)(F)(F)F.C1C[N+]2(CC[N+]1(CC2)CCl)F
Properties
Chemical formula	C7H14B2ClF9N2
Molar mass	354.26 g/mol
Appearance	colourless solid
Melting point	234
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) or Selectfluor, a trademark of Air Products and Chemicals, is a reagent in chemistry that is used as a fluorine donor. This compound is a derivative of the heterocycle DABCO . This colourless salt was first described in 1992 and has since been commercialized for use in organofluorine chemistry for electrophilic fluorination.

Preparation

Selectfluor is synthesized by the N-alkylation of diazabicyclo[2.2.2]octane (DABCO) with dichloromethane, followed by ion exchange with sodium tetrafluoroborate (replacing the chloride counterion for the tetrafluoroborate). Finally, this salt is treated with elemental fluorine and sodium tetrafluoroborate:

F-TEDA-BF4 synthesis

Applications

The conventional source of "electrophilic fluorine", i.e. the equivalent to the superelectrophile F⁺, is gaseous fluorine, which requires specialised equipment for manipulation. Selectfluor reagent is a salt, the use of which requires only routine procedures. Like F₂, the salt delivers the equivalent of F⁺. It is mainly used in the synthesis of organofluorine compounds:

The ability of Selectfluor to transfer fluorine to alkyl radicals has recently been demonstrated.

Specialized applications

Selectfluor reagent also serves as a strong oxidant, a property that is useful in other reactions in organic chemistry. Oxidation of alcohols and phenols. As applied to electrophilic iodination, Selectfluor reagent activates the I–I bond in I₂ molecule.

Other References

1. Lal, G. S., J. Org. Chem. 1993, 58, 2791.
2. Lal, G. S., Synth. Commun. 1995, 25 (5), 725.
3. Banks, R. E.; Lawrence, N. J.; Popplewell, A. L., J. Chem. Soc., Chem. Commun. 1994, 343.
4. Banks, R. E., J. Fluorine Chem. 1998, 87, 1.
5. Zupan, M.; Iskra, J.; Stavber, S., J. Fluorine Chem., 1995, 70, 7.
6. Matthews, D.P.; Miller, S. C.; Jarvi E. T.; Sabol, J. S.; McCarthy, J. R., Tettrahedron Lett. 1993, 34 (19), 3057.
7. Brunaus, M.; Dell, C. P.; Owton, W. M., J. Fluorine Chem. 1994, 201.
8. McClinton, M. A. ; Sik, V., J. Chem. Soc., Perkin Trans. I, 1992, 1891.
9. Hodson, H. F.; Madge, D. J.; Slawin, A. N. Z.; Widdawson, D. A.; Williams, D. J., Tetrahedron, 1994, 50 (6), 1899.
10. Stavber, S.; Zupan, M., J. Chem. Soc., Chem. Commun. 1994, 149.
11. Stavber, S.; Sotler, J.; Zupan, M., Tettrahedron Lett. 1994, 35 (7), 1105.

Patents

• US 5459267  "1-substituted-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts and their application as fluorinating agents"
• US 55227493  "Fluorinated Sulfonamide Derivatives"
• US 5086178  "Fluorinated Diazabicycloalkane Derivatives"
• US 5473065  "Fluorinated Diazabicycloalkane Derivatives"
• US 5442084  "Method of Selective Fluorination"