Reductive ring opening reactions of diphenyldihydrofullerenylpyrroles

Authors

William Hawkins, University of WollongongFollow
Paul A. Keller, University of WollongongFollow
Stephen G. Pyne, University of WollongongFollow

RIS ID

21134

Publication Details

Hawkins, W., Keller, P. A. & Pyne, S. G. (2007). Reductive ring opening reactions of diphenyldihydrofullerenylpyrroles. Tetrahedron Letters, 48 (42), 7533-7536.

Abstract

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.