A mild and general method for the synthesis of 5-substituted and 5,5-disubstituted fulleroprolines.
The reductive ring-opening of fullerenyldihydropyrrole yields ethyl N-benzhydryl fullerenyl[60]glycinate, which is deprotected to give ethyl fullerenylglycinate. The free amine is able to react with a variety of aldehydes and ketones in a Mannich-type process to produce 5-substituted and 5,5-disubstituted fulleroprolines and represents a versatile and general strategy to this class of compounds.
Thayumanavan
Rajeswari
R
School of Chemistry, University of Wollongong, Wollongong, New South Wales, 2522, Australia.
Hawkins
Bill C
BC
Keller
Paul A
PA
Pyne
Stephen G
SG
Ball
Graham E
GE
D037741:Fullerenes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011392:Proline / Q000138:chemical synthesis* / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization
D037741:Fullerenes; D011392:Proline