| Autor: |
Bacher EP; Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, United States., Koh KJ; Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, United States., Lepore AJ; Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, United States., Oliver AG; Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, United States., Wiest O; Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, United States., Ashfeld BL; Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, United States. |
| Abstrakt: |
A phosphorus(III)-mediated dearomatization of ortho -substituted dianiline squaraine dyes results in an unusual skeletal rearrangement to provide exotic, highly conjugated benzofuranone and oxindole scaffolds bearing a C3 side chain comprised of a linear conflagration of an enol, a phosphorus ylide, and 2,4-disubstituted aniline. Employing experimental and computational analysis, a mechanistic evaluation revealed a striking dependence on the acidity of the aniline ortho substituent. Notably, the rearrangement adducts underwent rapid and complete reversion to the parent squaraine in the presence of a Brønsted acid. |
