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+ Biochemistry
+ Redox
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Khang Nhat

Fluorination with xenon difluoride

Brian Dave  Follow

The reaction as pictured above is incorrect, the nitro group is not reduced. As you suggest this is (predominantly) an electrophilic aromatic substitution reaction.

Usually $\ce{HF}$ is used as a catalyst in these reactions and the following equilibrium is established.

$$\ce{XeF2 + HF <=> XeF+ + HF2^-}$$

The electrophilic $\ce{XeF^+}$ is the reactive species forming a complex with the aromatic ring. Xenon is expelled from the complex and the reaction proceeds to yield the meta-fluoro isomer as expected for an electrophilic aromatic substitution. Some other products, such as substituted biphenyls, are usually formed in small amounts suggesting that some minor pathway (radical-cation?) is also in play.

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