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NH4I-Promoted and H2O-Controlled Intermolecular Bis-sulfenylation and Hydroxysulfenylation of Alkenes via a Radical Process.

08:00 EDT 11th June 2019 | BioPortfolio

Summary of "NH4I-Promoted and H2O-Controlled Intermolecular Bis-sulfenylation and Hydroxysulfenylation of Alkenes via a Radical Process."

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.

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This article was published in the following journal.

Name: The Journal of organic chemistry
ISSN: 1520-6904
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Alkenes with the general formula H2C=CH-CH2-R.

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