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ChemInform Abstract

The thermal rearrangement of the vinyl ethers (I)/(II) gives syn/anti mixtures of the keto esters (III) and (IV). In the presence of a mercury catalyst, only double bond isomerization is observed. When a Pd catalyst is used, the (E,E) isomers (I) rearrange at 25°C to anti (III) (boatlike transition state), whereas at 150°C the (Z,E) isomers (II) give (III) (chairlike transition state).