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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 36, 2006 - Issue 23
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Original Articles

A Closer Look at the Hydroiodination of Propiolic Acid

James P. Donahue Department of Chemistry, Tulane University, New Orleans, Louisiana, USACorrespondence[email protected]
Pages 3461-3471 | Received 19 Apr 2006, Published online: 24 Nov 2006
 
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Abstract

The crystal structures of cis‐3‐iodoacrylic acid (1), trans‐3‐iodoacrylic acid (2), trans‐3‐iodoacrylic acid methyl ester (3), 3,3‐diiodopropanoic acid (4), and trans‐2,3‐diiodoacrylic acid (5) are reported. Compounds 1 and 2 are the kinetic and thermodynamic products, respectively, of the hydroiodination of propiolic acid. Compound 4 results from addition of a second equivalent of hydroiodic acid to 1 or 2, whereas 5 results from the addition of trace elemental iodine to propiolic acid.

Acknowledgments

The author thanks Professors F. A. Cotton and C. A. Murillo of Texas A&M University for hospitality and helpful discussions.

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