An NHI-promoted and HO-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 of alkenes to give a carbon-centered radical and immediately cyclize to a thiiranium ion, followed by combination with HO to afford β-hydroxysulfides in 52-89% yields with chemo- and regioselectivities. In the absence of water, 1,2-disulfenylation takes place to give bis-methylsulfane in moderate to good yields.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.9b01047 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Interconversion of Yeast Mating Types III. Action of the Homothallism (HO) Gene in Cells Homozygous for the Mating Type Locus.
Genetics
March 1977
Institute of Molecular Biology and Department of Biology, University of Oregon, Eugene, Oregon 97403.
Mating type interconversion in homothallic Saccharomyces cerevisiae has been studied in diploids homozygous for the mating type locus produced by sporulation of a/a/a/alpha and a/a/alpha/alpha tetraploid strains. Mating type switches have been analyzed by techniques including direct observation of cells for changes in alpha-factor sensitivity. Another method of following mating type switching exploits the observation that a/alpha cells exhibit polar budding and a/a and alpha/alpha cells exhibit medial budding.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!