lactonization mechanism


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  • What are the methods of lactone synthesis?

    Many methods adopted for ester synthesis can be applied for Lactone synthesis.
    Methods include Shiina macro-lactonization, nucleophilic abstraction and Yamaguchi esterification.
    Lactones like γ-nonalactone,γ-octalactone, γ-undecalactone, γ-decalactone can be synthesised in a single step process.

  • Mechanism: Lactones are cyclic esters and readily and irreversibly hydrolyze in alkaline media to produce a hydroxycarboxylate.
    Although carboxylic acids are weak acids they are completely ionized in basic media.

  • What is the halo lactonization reaction?

    The halolactonization reaction is one of the most common electrophilic addition reactions to alkenes.
    The mechanism is generally viewed as a two-step pathway, which involves the formation of an ionic intermediate, in most cases a haliranium ion.

  • What is the mechanism of lactone formation?

    Lactones are formed by intramolecular esterification of the corresponding hydroxycarboxylic acids, which takes place spontaneously when the ring that is formed is five- or six-membered.
    Lactones with three- or four-membered rings (α-lactones and β-lactones) are very reactive, making their isolation difficult.

  • The proposed mechanism involves the intermediacy of the corresponding aldehyde resulting from a retro-aldol cleavage of the dicyanovinyl group; this aldehyde can then undergo an intramolecular aldol reaction with the enolate <1983BCJ1219> (Scheme 64).
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