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Reaction of cyclohexene with a peroxy acid like mCPBA gives an epoxy acid according to Prilezhaev Reaction. I think it should work with any per acid according to the Mechanism here. But HCO3H gives anti diols, as given in my textbook. Is hydrolysis of epoxide going on?

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  • $\begingroup$ $\ce{H2CO3}$ is not a peracid. $\endgroup$
    – Maurice
    Feb 11 at 16:50
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    $\begingroup$ @Maurice I think the OP is refering to performic acid as epoxidation reagent $\endgroup$
    – Waylander
    Feb 11 at 17:31
  • $\begingroup$ @OscarLanzi performic acid is moderately oil-soluble according to this paper pubs.acs.org/doi/pdf/10.1021/acs.iecr.1c02212 $\endgroup$
    – Waylander
    Feb 11 at 22:20

2 Answers 2

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According to this patent

Performic acid is unsatisfactory as an epoxidizing agent for cyclohexene because the reaction leads preferentially to hydroxy-formoxy cyclohexane with small amounts and thus very low yields of the desired cyclohexene oxide.

So the initial nucleophilic species is formate anion which will readily hydrolyse in work-up

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If making cyclohexene oxide is desired, there are better methods than trying performic acid with its potential side reaction(s). The Wikipedia article suggests:

  • Industrially, using a heterogeneously catalyzed reaction, such as combining cyclohexene with oxygen on silver.

  • In the laboratory, using magnesium monoperoxyphthalate, $\ce{Mg^{2+}}\ce{[o-C6H4(CO2^-)(C(O)O2^-)]}$, as the active oxygen source.

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