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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 ...
EPFL2006
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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 ...
Efficient methods for the stereoselective synthesis of polyfunctional (E)- and (2)-alkenes and conjugated (EE)- and (E,2)-dienones are presented. They rely upon one-pot, four-component processes that condense 1-oxy-1,3-dienes, silyl enol ethers, SO2, and c ...
At low temperature and in the presence of an acid catalyst, SO2 adds to 1,3-dienes equilibrating with the corresponding 3,6-dihydro-1,2-oxathiin-2-oxides (sultines). These compounds are unstable above -60 degrees C and equilibrate with the more stable 2,5- ...
De Gruyter2008
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Alcohols, phenols and carboxylic acids are silylated with very good yields in the presence of silyl methallylsulfinates under non- basic conditions and with the formation of volatile co-products. ...