Kinetics and Mechanism of the Cyanoethylation of Alcohols

Ben Ami Feit, Albert Zilkha

Research output: Contribution to journalArticlepeer-review

Abstract

The kinetics of the cyanoethylation of alcohols using lithium, sodium, and potassium alkoxide catalysts have been measured in the derived alcohol as solvent at various temperatures. The reaction is first order in acrylonitrile and alkoxide anion. The rate of reaction is independent of the alkali metal and increases with increase of the basic strength of the alkoxide anion as follows: isopropoxide > n-butoxide = n-propoxide > ethoxide > methoxide. It increases with decrease in the dielectric constant in methanol-dioxane mixtures. All this is in accordance with a mechanism involving a slow rate determining nucleophilic attack of alkoxide anion on acrylonitrile. The nucleophile is shown to be RO- and not ROH.

Original languageEnglish
Pages (from-to)406-410
Number of pages5
JournalJournal of Organic Chemistry
Volume28
Issue number2
DOIs
StatePublished - 1 Feb 1963
Externally publishedYes

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