Crystal structure of (±)-(3aR,5R,8bR)-5-hydroperoxy-2-phenyl-6-tosyl-4,5,6,8b-tetrahydropyrrolo[3,4-e]indole-1,3(2H,3aH)-dione

Wayland E. Noland, Glen C. Gullickson, Rozalin R. Dickson, Leah L. Groess, Kenneth J. Tritch

Research output: Contribution to journalArticlepeer-review

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The title compound, C23H20N2O6S, crystallizes as a racemate in the space group P-1, with an overall L- or J-shape to each molecule. Centrosymmetric pairs of molecules are tandem hydrogen bonded between the hydroperoxy H atom and carbonyl O atom. A different centrosymmetric pairing has stacked S-tolyl rings, and a third pairing is L,J-interlocked by the short leg. Except for stacked tolyl pairs, neighboring π-systems are much closer to orthogonal than coaxial. The title compound is the first example of a hydroperoxide obtained from the autoxidation of a Diels-Alder adduct of a 2-vinylpyrrole.

Original languageEnglish (US)
Pages (from-to)192-195
Number of pages4
JournalActa Crystallographica Section E: Structure Reports Online
Issue number10
StatePublished - Oct 1 2014


  • autoxidation
  • crystal structure
  • cycloaddition
  • hydroperoxide
  • indole
  • pyrrole


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