Fullerene lipids: synthesis of novel nitrogen-bridged.
Reactions of methyl 6-azido-hexanoate, 8-azidooctanoate, and 12-azido-dodecanoate with [60]fullerene (1) gave the corresponding aza-[60]fullerene ester derivatives (2a-2c, 22-35% based on the amount of [60]fullerene reacted). The nitrogen atom is bonded to the [60]fullerene cage to yield a "[5,6]-open" type aza substructure. This was confirmed by the appearance of 30-31 sp2 signals at deltac 133-147 in the carbon nuclear magnetic resonance spectra. Reaction of methyl 11-azido-7-undecynoate with [60]fullerene furnished a mixture of aza-[60]fullerene (2d, 53%) and aziridine-[60]fullerene (2e, 38%) ester derivatives. Compound 2e was identified as the "[6,6]-closed" type aziridine-[60]fullerene derivative, which displayed 10 sp2 signals in the region deltac 140-145 and one signal at deltac 85.05 for the sp3 carbons of the cage. Refluxing a solution of compound 2d in toluene for 50 h gave about 50% yield of compound 2e, but not vice versa.
Jie
M S
MS
Department of Chemistry, The University of Hong Kong, SAR, China. hrsclkj@hkucc.hku.hk
Cheung
S W
SW
Ho
J C
JC
D001388:Aziridines / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D037741:Fullerenes; D008055:Lipids / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D009584:Nitrogen / Q000737:chemistry*; D014050:Toluene / Q000737:chemistry
D001388:Aziridines; D004952:Esters; D037741:Fullerenes; D008055:Lipids; D014050:Toluene; C033132:aziridine; D002244:Carbon; D009584:Nitrogen; C069837:fullerene C60