Fritsch–Buttenberg–Wiechell rearrangement of magnesium alkylidene carbenoids leading to the formation of alkynes
A series of 1-heteroatom-substituted vinyl <i>p</i>-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 <i>p</i>-tolyl su...
Main Authors: | , , , |
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Format: | Article |
Language: | English |
Published: |
Beilstein-Institut
2021-05-01
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Series: | Beilstein Journal of Organic Chemistry |
Subjects: | |
Online Access: | https://doi.org/10.3762/bjoc.17.94 |
Summary: | A series of 1-heteroatom-substituted vinyl <i>p</i>-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 <i>p</i>-tolyl sulfoxide and isopropylmagnesium chloride was optimal for this purpose. A variety of 1-chlorovinyl <i>p</i>-tolyl sulfoxides were prepared from carbonyl compounds and chloromethyl <i>p</i>-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 <sup>13</sup>C-labeled sulfoxides and by using DFT calculations. |
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ISSN: | 1860-5397 |