silver(I) salts of carboxylic acids react with halogens to give unstable
intermediates which readily decarboxylate thermally to yield alkyl
halides. The reaction is believed to involve homolysis of the C-C bond
and a radical chain mechanism.
Mechanism of the Hunsdiecker Reaction
Silver-Catalyzed Decarboxylative Chlorination of Aliphatic Carboxylic Acids
Z. Wang, L. Zhu, F. Yin, Z. Su, Z. Li, C. Li, J. Am. Chem. Soc., 2012,
Catalytic Hunsdiecker Reaction of α,β-Unsaturated Carboxylic Acids: How
Efficient Is the Catalyst?
J. Prakash, S. Roy, J. Org. Chem.,
2002, 67, 7861-7864.
Stereoselective Synthesis of (E)-β-Arylvinyl Bromides by
Microwave-Induced Hunsdiecker-Type Reaction
C. Kuang, Q. Yang, H. Senboku, M. Tokuda, Synthesis, 2005,