Add time:08/12/2019         Source:sciencedirect.com

Publisher SummaryThis chapter discusses properties and synthesis of certain fluorine-containing carboxylic acids. Abridged survey of organic chemical mechanisms related both to chemical behavior of fluoro carboxylic acids and to their syntheses is included in this chapter. The fate of the C-F bond in hydroxyfluorocarboxylie acids is intimately connected with the stability of the OH group. The mechanism of the intramolecular displacement is related to the inductive effect of F, rendering the H on OH more acidic. Intramolecular hydrogen bonding also contributes to the acidity of the hydroxyl. The simplest and best-known effect of the fluoro group on neighboring groups is due to its electron withdrawal by negative induction. Most fluorocarboxylic acids of biochemical interest are synthesized from ethyl fluoroacctates as starting material. The sequence of syntheses is illustrated. Fluoroacetic ester is replaced by difluoroacetic ester yielding the corresponding difluoro derivative. Self-condensation of fluoroacetic and fluorooxaloacetic esters gives the 2, 4-difluoro derivatives.

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