The reductive ring opening reaction conditions for the simple 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.
Life Sciences Commons, Physical Sciences and Mathematics Commons, Social and Behavioral Sciences Commons
Hawkins, W., Keller, P. A. & Pyne, S. G. (2007). Reductive ring opening reactions of diphenyldihydrofullerenylpyrroles. Tetrahedron Letters, 48 (42), 7533-7536.