Remote Substituent Effects on the Cheletropic and Homocheletropic Additions of Sulfur-Dioxide to Exocyclic Polyenes Grafted onto Bicyclo[2.2.2]Octane Skeletons
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A new one-pot synthesis of sulfoxides is presented. It involves the bora-ene reaction of sulfur dioxide and prop-2-ene-1-boronic esters, giving mixed anhydrides of sulfinic and boric acids. The latter react chemoselectively at the sulfur center with Grigna ...
Under appropriate conditions sulfur dioxide reacts with 1,3-dienes in a hetero-Diels-Alder fashion. In the case of 1-alkoxy-1,3-dienes the 6-alkoxy-3,6-dihydro-1,2-oxathiin-2-oxides (sultines) so-obtained can be ionized in the presence of Lewis or protic a ...
Sulphur dioxide reacts with 1-oxydienes generating zwitterions which are quenched by enoxysilanes to form substituted silyl alkenylsulfinates. These intermediates are desilylated with Bu4NF and the resulting sulfinates react with MeI giving the correspondi ...
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In the presence of a Lewis or protic acid and at low temperature, 1,3-dioxy-1,3-dienes add to sulfur dioxide generating zwitterionic intermediates that can react with carbon nucleophiles such as allylsilanes. After a retro-ene elimination of SO2, valuable ...
2-Methylprop-2-ene-1-sulfonyl fluorides can be easily prepared via the ene reaction of methallylsilanes and SO2. In the presence of a base, aldehydes and 2-methylprop-2-ene-1-sulfonyl fluorides give 1.3-(E) and (Z)-dienes. Their (Z) --> (E) isomerization b ...
Under appropriate conditions sulfur dioxide reacts with 1,3-dienes in the hetero-Diels-Alder fashion. In the case of 1-alkoxy-1,3-dienes the 6-alkoxy-3,6-dihydro-1,2-oxatiin-2-oxides (sultines) so-obtained can be ionized in the presence of Lewis or protic ...
The goal of this thesis was to open a new route to the synthesis of conjugated trienes using a new SO2-based C-C bond forming reactions developed in Lausanne. In addition, the potential of SO2 for applications in synthetic organic chemistry has been exploi ...
At low temperature, 1-alkoxy-1,3-dienes add to sulfur dioxide activated by a Lewis or protic acid generating zwitterionic intermediates that can be quenched by enoxysilanes. The resulting beta,gamma-unsaturated silyl sulfinates can be desilylated by 1:1 Pd ...
