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http://dx.doi.org/10.5012/bkcs.2006.27.8.1203

Oxidation of Aromatic Aldehydes with Tetrabutylammonium Fluoride:Competition with the Cannizzaro Reaction  

Chung, Kyoo-Hyun (Department of Chemistry, Inha University)
Lee, Jae Hak (Department of Chemistry, Inha University)
Chi, Dae Yoon (Department of Chemistry, Inha University)
Moon, Byung-Chul (Department of Chemistry, Inha University)
Lim, Choong Hwan (Department of Chemistry, Inha University)
Kim, Jin Pil (Department of Chemistry, Inha University)
Publication Information
Bulletin of the Korean Chemical Society / v.27, no.8, 2006 , pp. 1203-1205 More about this Journal
Abstract
During the synthesis of 4-fluorobenzaldehyde via the SNAr reaction of 4-nitrobenzaldehyde with TBAF, it was found that an equivalent amount of TBAF could oxidize benzaldehyde to benzoic acid. The reaction of 4-nitrobenzaldehyde with tetrabutylammonium fluoride (TBAF) gave 4-nitrobenzoic acid in high yield. Depending on the reaction conditions, other aromatic aldehydes produced acids with fewer amounts of alcohols. However, this type of oxidation has limited practical applications. Nevertheless, the mechanism is quite different from the Cannizzaro reaction because the amounts of the acid salt and alcohol formed were different.
Keywords
Oxidation; Tetrabutylammonium fluoride; Nucleophilicity of hydride; Cannizzaro reaction; Aromatic aldehyde;
Citations & Related Records
Times Cited By KSCI : 3  (Citation Analysis)
Times Cited By Web Of Science : 9  (Related Records In Web of Science)
Times Cited By SCOPUS : 9
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