The Journal of Organic Chemistry

Organic Syntheses with Anion Exchange Resins. I. The Malonic Ester Synthesis and Related Reactions

K Shimo, S Wakamatsu

Index: Shimo,K.; Wakamatsu,S. Journal of Organic Chemistry, 1963 , vol. 28, p. 504 - 506

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Citation Number: 15

Abstract

A quarternary ammonium hydroxide type of anion exchange resin, Amberlite IRA-400 (0H-j, was found to be an effective catalyst for the alkylation of ethyl malonate, ethyl cyanoacetate, or cyanoacetamide with various alkyl halides. It was found that the resin (OH-) rapidly exchanges its labile hydroxyl ion with the enolate of the active methylene compound even in aqueous solution producing the resin (R-) which could subsequently react with alkyl ...