Reductive ring opening reactions of diphenyldihydrofullerenylpyrroles

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Tetrahedron Letters, ISSN: 0040-4039, Vol: 48, Issue: 42, Page: 7533-7536

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Hawkins, William; Keller, Paul A; Pyne, Stephen G
Elsevier BV
Biochemistry, Genetics and Molecular Biology; Pharmacology, Toxicology and Pharmaceutics; Chemistry; Reductive; ring; opening; reactions; diphenyldihydrofullerenylpyrroles; CMMB; Life Sciences; Physical Sciences and Mathematics; Social and Behavioral Sciences
article description
The reductive ring opening reaction conditions for the simple [60]fullerenyldihydropyrrole 1 have been optimized to include acetic acid in the reaction mixture to rapidly protonate the anionic intermediate. Under these conditions, the ring opened dihydrofullerene 2 was obtained in 68% yield. Under slightly modified conditions and at −78 °C, the reductive bis-ring opening of the tethered trans -4 isomer 3 provided the novel racemic bis-dihydrofullerenyl derivative 7.