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- W2065376670 abstract "The palladium-catalyzed nucleophilic substitution of C-4-substituted 2-oxabicyclo[3.3.0]oct-7-en-3-ones (unsaturated, fused lactones) have been studied particularly in relation to how electronic and steric factors influenced the rate and efficiency of substitution reactions. Thus, a range of α-substituted lactones were prepared (X = H, Me, OH, OAc, Br, N3, NHCBZ) and subjected to palladium-catalyzed substitution reaction with diethyl sodiomalonate, and it was found that reaction rates increased with increasing electron-withdrawing ability of the substituent and that there was a strong correlation between rate and pKa of the corresponding substituted acetic acids (XCH2CO2H). The only exception to the correlation was with X = OH, in which case the endo isomer reacted considerably faster than expected and the exo isomer reacted much slower than expected. It was also found that the rates of reaction of the endo isomers were greater than the exo isomers. The increased rates have been accounted for by a shift i..." @default.
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- W2065376670 date "2010-08-02" @default.
- W2065376670 modified "2023-09-25" @default.
- W2065376670 title "ChemInform Abstract: Scope and Limitations in Palladium-Catalyzed Substitution Reactions of Unsaturated Fused Lactones." @default.
- W2065376670 cites W2952451348 @default.
- W2065376670 doi "https://doi.org/10.1002/chin.199749131" @default.
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