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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 20
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Original Articles

The One-Pot Synthesis and Diels-Alder Reactivity of 2,5-Dihydrothiophene- 1,1-dioxide-3-carboxylic Acid

Genara S. Andrade School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia, USA
,
Joachim E. Berkner School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia, USA
,
Charles L. Liotta School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia, USA
,
Charles Eckert School of Chemical Engineering, Georgia Institute of Technology, Atlanta, Georgia, USA
,
David A. Schiraldi KoSa, Spartanburg, South Carolina, USA
,
Arthur Andersen DuPont, Experimental Station, Wilmington, Delaware, USA
&
David M. Collard School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia, USACorrespondence[email protected]
 show all
Pages 3643-3650 | Published online: 15 Aug 2006
 
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Abstract

A one-pot preparation of 2,5-dihydrothiophene-1,1-dioxide-3-carboxylic acid (3-sulfolene-3-carboxylic acid) is reported. The carboxylation of 3-sulfolene, exclusively at the 3-position, using CO2 and DBU proceeds to >90% conversion. A rapid workup gives 3-sulfolene-3-carboxylic acid, a stable precursor to 1,3-butadiene-2-carboxylic acid. High conversions to Diels-Alder adducts were obtained upon treatment of 3-sulfolene-3-carboxylic acid with various dienophiles.

Acknowledgment

We thank KoSa and DuPont for support of this research, along with the UNCF-Merck Science Initiative and the GEM Consortium for awards to G.S.A.

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