Structural reassignment of the mono- and bis-addition products from the addition reactions of N-(Diphenylmethylene)glycinate esters to [60]fullerene under Bingel conditions.
The addition of N-(diphenylmethylene)glycinate esters (Ph2C=NCH2CO2R) to [60]fullerene under Bingel conditions gives [60]fullerenyldihydropyrroles and not methano[60]fullerenyl iminoesters [C60C(CO2R)(N=CPh2)] as previously reported. Unequivocal evidence for the structure of C60C(CO2Et)(N=CPh2) was provided by INADEQUATE NMR studies on 13C enriched material. New mechanistic details are proposed to account for the formation of [60]fullerenyldihydropyrroles and their reductive ring-opening reactions.
Ball
Graham E
GE
NMR Facility, School of Chemistry, University of New South Wales, Sydney, New South Wales 2052, Australia.
Burley
Glenn A
GA
Chaker
Leila
L
Hawkins
Bill C
BC
Williams
James R
JR
Keller
Paul A
PA
Pyne
Stephen G
SG