Document Detail

Protonated Carbonic Acid and Reactive Intermediates in the Acidic Decarboxylation of Indole-Carboxylic Acids.
MedLine Citation:
PMID:  22804752     Owner:  NLM     Status:  Publisher    
Elucidation of the mechanism for decarboxylation of indole-carboxylic 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 an indole-carboxylic 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, and implicates PCA as a potential carboxylating reagent in the microscopic reverse reaction.
Adelle A Vandersteen; Scott O C Mundle; Ronald Kluger
Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-7-17
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  -     ISSN:  1520-6904     ISO Abbreviation:  -     Publication Date:  2012 Jul 
Date Detail:
Created Date:  2012-7-18     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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