Master Organic Chemistry Reaction Guide

Formation of epoxides from alkenes using m-CPBA

Description: meta-chloroperoxybenzoic acid (m-CPBA) or other peroxyacids such as peracetic acids will convert alkenes into epoxides.

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Real-Life Examples:

Org. Synth. 1928, 8, 102

DOI Link: 10.15227/orgsyn.008.0102

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Org. Synth. 1958, 38, 83

DOI Link: 10.15227/orgsyn.038.0083

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Org. Synth. 1969, 49, 62

DOI Link: 10.15227/orgsyn.049.0062

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Org. Synth. 1977, 56, 1

DOI Link: 10.15227/orgsyn.056.0001

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Comment section

10 thoughts on “Formation of epoxides from alkenes using m-CPBA

  1. What happens if you have a cyclohexane with two double bonds combined with two equivalents of mCPBA? Does it epoxidate both bonds?

    1. This reaction doesn’t work with alkynes! Can you think why not? [hint – it has something to do with aromaticity]

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