Palladium-catalyzed isomerization of (Z)-1-functionalized-4-acetoxy-2-butenes: Solvent and substituent effects |
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| Authors: | Anna Maria Zawisza Jacques Muzart |
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| Affiliation: | a Department of Organic and Applied Chemistry, University of Lodz, ul. Narutowicza 68, 90-136 Lodz, Poland
b Institut de Chimie Moléculaire, CNRS-Université de Reims Champagne-Ardenne, UFR Sciences, Boîte no. 44, BP 1039, 51687 Reims Cedex 2, France |
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| Abstract: | The Pd(PPh3)4-catalyzed isomerization of (Z)-1,4-diacetoxy-2-butene, (Z)-1-(t-butyldimethylsilyloxy)-4-acetoxy-2-butene and (Z)-1-(t-butyldiphenylsilyloxy)-4-acetoxy-2-butene affords the corresponding (E)-isomers and 1,2-difunctionalized-3-butenes. In THF, the formation of the (E)-isomers is mainly due to reaction from an η1-allylpalladium intermediate while an η3-allylpalladium is the main key intermediate in DMF. The time to reach equilibrium between the products and their respective concentrations depend on the nature of the substituents and the solvent. |
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| Keywords: | Catalysis Allylpalladium Coordination modes 1,4-Difunctionalized-2-butenes Isomerization Solvent effects |
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