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Reactivity of a hypervalent iodine trifluoromethylating reagent toward THF: ring opening and formation of trifluoromethyl ethers. | LitMetric

AI Article Synopsis

  • The compound 1-Trifluoromethyl-1,2-benziodoxol-3-(1H)-one can transfer a CF(3) group to the oxygen of THF (tetrahydrofuran) when a Lewis or Bronsted acid is present.
  • This leads to a new reaction where THF opens up to form trifluoromethyl ethers.
  • The text discusses the details of this reaction and provides insights into how reagent 1 works mechanism-wise.

Article Abstract

1-Trifluoromethyl-1,2-benziodoxol-3-(1H)-one (1) is able to transfer the electrophilic CF(3) group to the oxygen atom of THF in the presence of a Lewis or Bronsted acid. This results in a new ring-opening reaction of THF yielding trifluoromethyl ethers. Details of this reaction and the insight gained into the mechanism of action of reagent 1 are reported.

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Source
http://dx.doi.org/10.1021/jo9025429DOI Listing

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