Protonated carbonic acid and reactive intermediates in the acidic decarboxylation of indolecarboxylic acids.

2012 
Elucidation of the mechanism for decarboxylation of indolecarboxylic acids over a wide range of solution acidity reveals the importance of protonated carbonic acid (PCA) as a reaction intermediate. In concentrated acid, the initial addition of water to the carboxyl group of the indolecarboxylic acid leads to a hydrated species that is capable of releasing PCA upon rate-determining carbon–carbon bond cleavage. The overall process is catalytic in water and acid, implicating PCA as a potential carboxylating reagent in the microscopic reverse reaction.
    • Correction
    • Source
    • Cite
    • Save
    • Machine Reading By IdeaReader
    29
    References
    16
    Citations
    NaN
    KQI
    []