The Malonic Ester Synthesis with Styrene Oxide and with Butadiene Oxide
1. The condensation of styrene oxide and of butadiene oxide with sodium malonic ester, followed in each case by hydrolysis and decarboxylation, has been found to yield γ-phenyl-γ-butyrolactone and γ-vinyl-γ-butyrolactone, respectively. The fact that no other lactone could be isolated in either case indicates that the attack of the nucleophilic anion of malonic ester occurs exclusively at the terminal (unsubstituted) carbon atom of the epoxide ring. 2. On the basis of the direction of epoxide ring opening in the reaction of styrene oxide and of butadiene oxide with sodium malonic ester, the generalization that the phenyl and vinyl groups always exhibit a -Is effect as compared with the hydrogen atom, appears unjustified.
R. R. Russell and C. A. VanderWerf, "The Malonic Ester Synthesis with Styrene Oxide and with Butadiene Oxide," Journal of the American Chemical Society, American Chemical Society (ACS), Jan 1947.
The definitive version is available at https://doi.org/10.1021/ja01193a003
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© 1947 American Chemical Society (ACS), All rights reserved.