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Catalytic Hunsdiecker Reaction of α,β-Unsaturated Carboxylic Acids: How Efficient Is the Catalyst?

Jaya Prakash Das and Sujit Roy*

*Organometallics & Catalysis Laboratory, Chemistry Department, Indian Institute of Technology, Kharagpur 721302, India, Email:

J. Prakash, S. Roy, J. Org. Chem., 2002, 67, 7861-7864.

DOI: 10.1021/jo025868h


Using triethylamine as catalyst in Hunsdiecker reactions with N-halosuccinimides as Br+ or I+ source, cinnamic acids, and propiolic acids are converted to the corresponding α-halostyrenes and 1-halo-1-alkynes in good isolated yields within 1-5 min.

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Key Words

N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, Hunsdiecker Reaction, α-chloroalkenes, α-bromoalkenes, α-iodoalkenes, 1-bromo-1-alkynes, 1-iodo-1-alkynes

ID: J54-Y2002-1750