Cycloaddition reaction of 1-(4-nitrophenyl)-3-phenylnitrile ylide to buckminsterfullerene[60]

Benzylamine imines as versatile precursors to azomethine and nitrile ylides in the [2 + 3] cycloaddition reactions with [60]fullerene

“…7 The 1 H NMR shifts were the same to within ±0.05 ppm except for the resonances of protons neighbouring to the NO 2 groups that were strongly affected by solvent and concentration. The only detected sp 3 -carbon signal was at 87.45 ppm, which is comparable to 87.74 ppm reported for 3c''.…”

“…11 Therefore, we can doubt the preparation and isolation of the open-caged pyrrolinofullerene 3c'' reported earlier. 7 The 600 MHz 1 H NMR spectrum evidenced the presence of two 4-nitrophenyl groups in 3c', as well as all signals expected for 2c. The 150 MHz 13 C NMR spectrum revealed three sp 3 -carbon signals at 84-89 ppm, as expected for the structure of 3c' along with a set of four minor signals at 74-78 ppm corresponding to the sp 3 carbons of 2c.…”

New pyrrolidine and pyrroline derivatives of fullerenes: from the synthesis to the use in light-converting systems

“…55 All these methods have certain drawbacks because either the starting compounds are difficult to prepare or the reactions have a limited synthetic application. Hence, the in situ oxidation of readily available benzylamine based imines to nitrile ylides can be used as a convenient method for the synthesis of pyrrolinofullerenes.…”

Chemistry of heterocyclic compounds at the Department of Organic Chemistry, Chemical Faculty, M. V. Lomonosov State University. (Review)

“…A. Ovcharenko). The double bond in the open cycloadducts is located at the α-position in relation to the unsubstituted phenyl ring, whereas in the [6,6]-closed isomer it is at the α-position in relation to the nitrophenyl substituent [63]. Thus, it was found for the first time that the cycloaddition of 1-(4-nitrophenyl)-3-phenylnitrile ylide, generated in situ from Nbenzyl-4-nitrophenylimidoyl chloride by the action of triethylamine, leads not only to the formation of [6,6]-closed 1,2-[3,4-dihydro-2-phenyl-5-(4-nitrophenyl)-2H-pyrrolo]fullerene [60] (1) but also to a mixture of diastereomeric [6,5]-open (2a, b) fulleroid cycloadducts in a ratio of 2:1.…”