Hunsdiecker-Type Bromodecarboxylation of Carboxylic Acids with Iodosobenzene Diacetate–Bromine

✍ Scribed by Pelayo Camps; Andrés E Lukach; Xavier Pujol; Santiago Vázquez

• Book ID: 104202606
• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 143 KB
• Volume: 56
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(00)00169-1

✦ Synopsis

AbstractÐCarboxylic acids are bromodecarboxylated in moderate to good yields on reaction with iodosobenzene diacetate and bromine under irradiation with a tungsten lamp. The reaction works very well with carboxylic acids having a primary, secondary or tertiary a-carbon atom, although diphenylacetic acid gives benzophenone. Benzoic acid derivatives are bromodecarboxylated in moderate yields if electronwithdrawing substituents are present in the benzene ring, while they are recovered mostly unchanged if the substituents are electrondonating. Partially iodinated products have been isolated in low yield from the bis-bromodecarboxylation of dicarboxylic acids having two bridgehead a-carbon atoms.