Beilstein J. Org. Chem.2021,17, 1352–1359, doi:10.3762/bjoc.17.94
treated with organometallic reagents to evaluate which combination of sulfoxides and organometallic reagents yielded alkynes the most efficiently. The use of 1-chlorovinylp-tolylsulfoxide and isopropylmagnesium chloride was optimal for this purpose. A variety of 1-chlorovinyl p-tolyl sulfoxides were
magnesium alkylidene carbenoids was studied by using 13C-labeled sulfoxides and by using DFT calculations.
Keywords: alkyne; 1-chlorovinylp-tolylsulfoxide; DFT calculation; Fritsch–Buttenberg–Wiechell rearrangement; magnesium alkylidene carbenoid; Introduction
Alkynes are important compounds in organic
)-substituted 1-chlorovinylp-tolylsulfoxide 2a was added to isopropylmagnesium chloride in toluene at −78 °C, and the mixture was warmed to 0 °C for 2 h (Table 1, entry 1). Excess isopropylmagnesium chloride (3.5 equivalents) was necessary for the complete consumption of the sulfoxide. As a result, isopropyl
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Graphical Abstract
Scheme 1:
Synthesis of alkynes from carbonyl compounds through one-carbon homologation.