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Updated: Aug 19, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
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Effect of cyclodextrin complexation in bromine addition to unsymmetrical olefins: evidence for participation of

Manickam C Durai Manickam1, Subramanian Annalakshmi, Kasi Pitchumani

  • 1School of Chemistry, Madurai Kamaraj University, Madurai, 625 021, INDIA.

Organic & Biomolecular Chemistry
|March 8, 2005
PubMed

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In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.