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An NH4I-promoted and H2O-controlled intermolecular difunctionalization of alkenes for the synthesis of bis-methylsulfane and β-hydroxysulfides is presented. Mechanistic investigation revealed the reaction proceeds via methylthiyl radical addition to C=C double bond of alkenes to give a carbon-centered radical and immediately cyclize to a thiiranium ion, followed by combination with H2O to afford β-hydroxysulfides in 52-89% yield with chemo- and regioselectivity. In the absence of the water, 1,2-disulfenylation takes place to give bis-methylsulfane in moderate to good yields.
This article was published in the following journal.
Name: The Journal of organic chemistry
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The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.
Alkenes with the general formula H2C=CH-CH2-R.
Inorganic salts of HYDROGEN CYANIDE containing the -CN radical. The concept also includes isocyanides. It is distinguished from NITRILES, which denotes organic compounds containing the -CN radical.
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Unsaturated hydrocarbons of the type Cn-H2n, indicated by the suffix -ene. (Grant & Hackh's Chemical Dictionary, 5th ed, p408)