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 sroy@chem.iitkgp.ernet.in
J. Org. Chem., 2002, 67 (22), pp 7861–7864
DOI: 10.1021/jo025868h
Publication Date (Web): October 3, 2002
Copyright © 2002 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

Abstract Image

UV−vis spectrophotometry is utilized to measure the relative efficiency of lithium acetate, tetrabutylammonium trifluoroacetate, and triethylamine as catalysts for the conversion of 4-methoxycinnamic acid to 4-methoxy-β-bromostyrene. In acetonitrile−water as solvent, the efficiency order is lithium acetate > triethylamine > tetrabutylammonium trifluoroacetate. For triethylamine as catalyst, solvent-dependent order is acetonitrile−water > dichloromethane > acetonitrile. Using triethylamine as catalyst (5−20 mol %), cinnamic acids, and propiolic acids are converted to corresponding β-bromostyrenes and 1-halo-1-alkynes in 60−98% isolated yields within 1−5 min.

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History

  • Published In Issue November 01, 2002
  • Received April 28, 2002

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