Mass spectrometry, fullerene adducts

Similarly, other cycloadducts of nitrile oxides with C6o were synthesized. The cycloadducts were characterized by 13C NMR spectroscopy and high-resolution fast atom bombardment (FAB) mass spectrometry. It should be mentioned that X-ray structure determination of the 3-(9-anthryl)-4,5-dihydroisoxazole derivative of C6o, with CS2 included in the crystals, was achieved at 173 K (255). Cycloaddition of fullerene C60 with the stable 2-(phenylsulfonyl)benzonitrile oxide was also studied (256). Fullerene formed with 2-PhSC>2C6H4CNO 1 1 and 1 2 adducts. The IR, NMR, and mass spectra of the adducts were examined. Di(isopropoxy)phosphorylformonitrile oxide gives mono- and diadducts with C60 (257). Structures of the adducts were studied using a combination of high performance liquid chromatography (HPLC), semiempirical PM3 calculations, and the dipole moments. 

So far, all efforts to generate, isolate and characterize heterofuUerenes via Kratsch-mer-Huffman vaporization of graphite in the presence of hetero-element-containing compounds such as boron nitride (BN) or cyanogen (CN)2 have failed. An alternative route for the direct formation of heterofuUerenes is cluster rearrangement within exohedral fullerene derivatives such as iminofullerenes and azafuUeroids. The first hints of success by this approach were obtained from mass spectrometry investigations of the cis-l-diazabishomo[60]fullerene 3 [12], the n-butylamine adduct 4 [12] the 1,2-epiminofullerene 5 [11] and the cluster opened ketolactam 6 [2]. 

The [2-1-1] fragmentation of the precursors shown in Figure 6.2 also provides a potential route to monocyclic carbon clusters. Thus cyclic dehydro oligomers of diethynyl[4.4.1]propellatetraenes 6a,b incorporated in a fullerene structure have been prepared and their fragmentation was investigated by mass spectrometry [7]. MALDI TOF mass spectra of 6a,b exhibited peaks due to the stepwise loss of the fullerene fragments, leading to the formation of mono-fullerene adducts of C15 and C20. However, the... 

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