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The reaction of F 2 with organic compounds is, however, highly exothermic and can lead to non-selective fluorinations and C–C cleavage, as well as explosions. [6] Only a few selective radical fluorination methods have been reported. [7] [8] The use of fluorine for radical fluorination is mainly limited to perfluorination reactions. [5]
The direct fluorination of hydrocarbons with F 2, often diluted with N 2, is useful for highly fluorinated compounds: R 3 CH + F 2 → R 3 CF + HF. Such reactions however are often unselective and require care because hydrocarbons can uncontrollably "burn" in F 2, analogous to the combustion of hydrocarbon in O 2. For this reason, alternative ...
Reductive fluorination: 2 CrO 2 F 2 + XeF 2 → 2 CrOF 3 + Xe +O 2. Aromatic fluorination: Alkene fluorination: Radical fluorination in radical decarboxylative fluorination reactions, [10] in Hunsdiecker-type reactions where xenon difluoride is used to generate the radical intermediate as well as the fluorine transfer source, [28] and in ...
The mechanism of electrophilic fluorination remains controversial. At issue is whether the reaction proceeds via an S N 2 or single-electron transfer (SET) process. In support of the S N 2 mechanism, aryl Grignard reagents and aryllithiums give similar yields of fluorobenzene in combination with N-fluoro-o-benzenedisulfonimide (NFOBS), even though the tendencies of these reagents to ...
Trifluoromethyl hypofluorite is an organofluorine compound with the chemical formula C F 3 OF.It exists as a colorless gas at room temperature and is highly toxic. [1] It is a rare example of a hypofluorite (compound with an O−F bond).
Electrophilic fluorinating reagents could in principle operate by electron transfer pathways or an S N 2 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.
C 6 H 13 CO 2 H + 2 SF 4 → C 6 H 13 CF 3 + 2 SOF 2 + HF. The formation of the trifluoromethyl derivative sometimes competes with formation of tetrafluoroalkyl ethers, which arise from the reaction between difluoromethyl cation and acyl fluoride. [11] [12] Sulfur tetrafluoride can be used to fluorinate polymers efficiently.
The F 2 molecule is commonly described as having exactly one bond (in other words, a bond order of 1) provided by one p electron per atom, as are other halogen X 2 molecules. However, the heavier halogens' p electron orbitals partly mix with those of d orbitals, which results in an increased effective bond order; for example, chlorine has a ...