Selectfluor

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Selectfluor
Names
IUPAC name
1-(Chloromethyl)-4-fluoro-1,4-diazabicyclo[2.2.2]octane-1,4-diium ditetrafluoroborate
Other names
F-TEDA, N-Chloromethyl-N-fluorotriethylenediammonium bis(tetrafluoroborate)
1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)
Identifiers
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.101.349 Edit this at Wikidata
EC Number
  • 414-380-4
UNII
  • 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
  • [B-](F)(F)(F)F.[B-](F)(F)(F)F.C1C[N+]2(CC[N+]1(CC2)CCl)F
Properties
C7H14B2ClF9N2
Molar mass 354.26 g/mol
Appearance colourless solid
Melting point 190 °C (374 °F; 463 K) decomposes >80 °C, exact m.p. is uncertain[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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 nucleophillic base DABCO. It is a colourless salt that tolerates air and even water. It has been commercialized for use for electrophilic fluorination.[1]

Preparation

F-TEDA-BF4 synthesis

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). The resulting salt is treated with elemental fluorine and sodium tetrafluoroborate:[2]

The cation is often depicted with one skewed ethylene ((CH2)2) group. In fact, these pairs of CH2 groups are eclipsed so that the cation has idealized C3h symmetry.

Mechanism of fluorination

Electrophilic fluorinating reagents could in principle operate by electron transfer pathways or an SN2 attack at fluorine. This distinction has not been decided.[2] By using a charge-spin separated probe,[3] it was possible to show that the electrophilic fluorination of stilbenes with Selectfluor proceeds through an SET/fluorine atom transfer mechanism.[4]

In certain cases Selectfluor can transfer fluorine to alkyl radicals.[5]

Applications

The conventional source of "electrophilic fluorine", i.e. the equivalent to the

organofluorine compounds:[2]

Specialized applications

Selectfluor reagent also serves as a strong oxidant, a property that is useful in other reactions in

electrophilic iodination, Selectfluor reagent activates the I–I bond in I2 molecule.[6]

Related reagents

Similar to Selectfluor are N-fluorosulfonimides:[7]

References

  1. ^
    ISBN 978-0471936237
    .
  2. ^
    PMID 15578736
    .
  3. ISSN 0022-3263
    .
  4. PMID 24376910
    .
  5. S2CID 196807570
    .
  6. ISSN 0039-7881
    .
  7. ISBN 978-0-471-26418-7
    .

Patents
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