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Epoxidation of alkenes

4 real reactions from the literature, on styrenes, tetrasubstituted six-membered cycloalkenes and tetrasubstituted four-membered cycloalkenes. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.

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  1. Epoxidation: 1,2-dimethyl-1,4-cyclohexadiene (a tetrasubstituted six-membered cycloalkene) with mCPBA; CHCl3, Δ gives 1,6-dimethyl-7-oxabicyclo[4.1.0]hept-3-ene (the epoxide).

  2. Epoxidation: trans-stilbene (a styrene) with peracetic acid, NaOAc; AcOH, CH2Cl2 gives the epoxide.

  3. Epoxidation: 1,2,3,4,5,6-hexamethylbicyclo(2,2,0)hexa-2,5-diene (a tetrasubstituted four-membered cycloalkene) with mCPBA; toluene, 0-25 °C gives the epoxide.

  4. Epoxidation: styrene with CHCl3, 0 °C gives styrene oxide (the epoxide).