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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 12
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Original Articles

Rearrangement of Indolinesulfonamides to Sulfones Using Polyphosphoric Acid (PPA)

Brian Raszka Department of Chemistry and Biochemistry, University of the Sciences in Philadelphia, Philadelphia, Pennsylvania, USA
,
James McKee Department of Chemistry and Biochemistry, University of the Sciences in Philadelphia, Philadelphia, Pennsylvania, USA
&
Murray Zanger Department of Chemistry and Biochemistry, University of the Sciences in Philadelphia, Philadelphia, Pennsylvania, USACorrespondence[email protected]
Pages 1837-1846 | Received 26 May 2009, Published online: 17 May 2010
 
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Abstract

Unlike other N-alkylsulfonanilides, indolinesulfonamides hydrolyze in 98% sulfuric acid. Recent work in this laboratory has shown that rearrangement can be achieved by using polyphosphoric acid. A series of substituted indolinesulfonamides has been prepared and rearranged to their corresponding indoline arylsulfones.

Notes

a Compound 3 is known: Ref. 7 (mp 129.5–131).

b Compound 4 is known: Ref 8 (mp 100.5–101.5).

c Compound 5 is known: Ref. 9 (no mp reported).

d Compound 8 is known: Ref. 10 (mp 75–77).

e Compound 11 is known: Ref. 11 (mp 135–136).

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