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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 46, 2016 - Issue 11
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Original Articles

Triflic acid–catalyzed rearrangement of unalkylated benzene sulfonanilides

Rebecca NewcomerDepartment of Chemistry and Biochemistry, University of the Sciences, Philadelphia, PA, USA
,
James McKeeDepartment of Chemistry and Biochemistry, University of the Sciences, Philadelphia, PA, USA
&
Murray ZangerDepartment of Chemistry and Biochemistry, University of the Sciences, Philadelphia, PA, USACorrespondence[email protected]
Pages 949-955 | Received 23 Mar 2016, Published online: 31 May 2016
 
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ABSTRACT

Previous work has demonstrated that alkylated benzene sulfonanilides undergo sulfuric acid (98%)–catalyzed rearrangement to alkylamino diaryl sulfones. Similar treatment of their unalkylated analogs typically leads only to hydrolysis. Surprisingly, when the unalkylated benzene sulfonanilides react with triflic acid, rearrangement to sulfones does occur.

GRAPHICAL ABSTRACT

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