AI Article Synopsis
- Researchers synthesized several vinyl-tolyl sulfoxides and tested them with different organometallic reagents to find the most efficient combination for producing alkynes.
- The best results came from using 1-chlorovinyl-tolyl sulfoxide with isopropylmagnesium chloride.
- They prepared various sulfoxides and investigated the mechanism of the resulting alkynes through C-labeling and DFT (Density Functional Theory) calculations, focusing on the FBW (Fritsch-Buttenberg-Wiechell) rearrangement process.
Article Abstract
A series of 1-heteroatom-substituted vinyl -tolyl sulfoxides were prepared and treated with organometallic reagents to evaluate which combination of sulfoxides and organometallic reagents yielded alkynes the most efficiently. The use of 1-chlorovinyl -tolyl sulfoxide and isopropylmagnesium chloride was optimal for this purpose. A variety of 1-chlorovinyl -tolyl sulfoxides were prepared from carbonyl compounds and chloromethyl -tolyl sulfoxide and were converted into alkynes via the sulfoxide/magnesium exchange reaction and subsequent Fritsch-Buttenberg-Wiechell (FBW) rearrangement of the resulting magnesium alkylidene carbenoids. The mechanism of the FBW rearrangement of magnesium alkylidene carbenoids was studied by using C-labeled sulfoxides and by using DFT calculations.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8182682 | PMC |
| http://dx.doi.org/10.3762/bjoc.17.94 | DOI Listing |
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