Beilstein J. Org. Chem.2021,17, 1352–1359, doi:10.3762/bjoc.17.94
magnesium alkylidene carbenoids was studied by using 13C-labeled sulfoxides and by using DFT calculations.
Keywords: alkyne; 1-chlorovinyl p-tolyl sulfoxide; DFT calculation; Fritsch–Buttenberg–Wiechell rearrangement; magnesiumalkylidenecarbenoid; Introduction
Alkynes are important compounds in organic
rearrangement of magnesium alkylidene carbenoids 3 by using 13C-labeled sulfoxides and by using DFT calculations is also described.
Results and Discussion
Synthesis of 1-heteroatom-substituted vinyl p-tolyl sulfoxides
As magnesiumalkylidenecarbenoid precursors, a series of 1-heteroatom-substituted vinyl p
group and methyl group to the carbenoid carbon atom was examined for each geometric isomer to locate the transition state [37]. While appropriate transition state structures were not found for the 1,2-shift of the methyl group in (E)-3e and the 1,2-shift of substituents in magnesiumalkylidenecarbenoid
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Graphical Abstract
Scheme 1:
Synthesis of alkynes from carbonyl compounds through one-carbon homologation.