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Updated: Sep 19, 2025

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
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Published on: September 8, 2013

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Regioselective Sulfonylation of Methylenecyclopropanes with Thianthrenium Salts Enabled by Electron Donor-Acceptor

Chao Li1, Yinghui Yang1, Xianyue Xiong1

  • 1Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education; Anhui Provincial Key Laboratory of Synthetic Chemistry and Applications; College of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui 235000, P. R. China.

The Journal of Organic Chemistry
|June 6, 2025
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.
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