Publications
2006
Brough Peter, Klumpp Cedric, Bianco Alberto, Campidelli Stephane, Prato Maurizio
[60]fullerene-pyrrolidine-N-oxides Article de journal
Dans: The Journal of Organic Chemistry, vol. 71, no. 5, p. 2014–2020, 2006, ISSN: 0022-3263.
Résumé | Liens | BibTeX | Étiquettes: Chromatography, Fullerenes, High Pressure Liquid, I2CT, Nitrogen, Oxidation-Reduction, Oxides, Pyrrolidines, Spectrum Analysis, Team-Bianco
@article{brough_60fullerene-pyrrolidine-n-oxides_2006,
title = {[60]fullerene-pyrrolidine-N-oxides},
author = {Peter Brough and Cedric Klumpp and Alberto Bianco and Stephane Campidelli and Maurizio Prato},
doi = {10.1021/jo052388s},
issn = {0022-3263},
year = {2006},
date = {2006-03-01},
journal = {The Journal of Organic Chemistry},
volume = {71},
number = {5},
pages = {2014--2020},
abstract = {Eight members of a new family of fullerene derivatives, [60]fulleropyrrolidine-N-oxides, have been synthesized and characterized. Facile oxidation, by a peracid, of the parent [60]fulleropyrrolidine gave clean conversions into the product molecules, in which the tertiary amine is transformed into a quaternary amine bearing an oxygen atom. The reaction is very selective, favoring the nitrogen atom of the pyrrolidine ring in preference to epoxidation of the fullerene cage. The 1H NMR shows an AB quartet splitting pattern, characteristic of nonequivalent hydrogens in the pyrrolidine ring and at a chemical shift displacement of 0.8 ppm downfield. Other methods of characterization are described, including MS, differential scanning calorimetry, thermogravimetric analysis, HPLC, UV/vis, and IR. Conclusive evidence for the formation of an N-oxide moiety is provided by the synthesis, oxidation, and NMR characterization of a novel [60]fulleropyrrolidine containing a 15N isotope, showing an 85 ppm downfield heteroatom chemical shift. Preliminary details of the effects of substitution on the reactivity of the pyrrolidine ring are also reported.},
keywords = {Chromatography, Fullerenes, High Pressure Liquid, I2CT, Nitrogen, Oxidation-Reduction, Oxides, Pyrrolidines, Spectrum Analysis, Team-Bianco},
pubstate = {published},
tppubtype = {article}
}
Eight members of a new family of fullerene derivatives, [60]fulleropyrrolidine-N-oxides, have been synthesized and characterized. Facile oxidation, by a peracid, of the parent [60]fulleropyrrolidine gave clean conversions into the product molecules, in which the tertiary amine is transformed into a quaternary amine bearing an oxygen atom. The reaction is very selective, favoring the nitrogen atom of the pyrrolidine ring in preference to epoxidation of the fullerene cage. The 1H NMR shows an AB quartet splitting pattern, characteristic of nonequivalent hydrogens in the pyrrolidine ring and at a chemical shift displacement of 0.8 ppm downfield. Other methods of characterization are described, including MS, differential scanning calorimetry, thermogravimetric analysis, HPLC, UV/vis, and IR. Conclusive evidence for the formation of an N-oxide moiety is provided by the synthesis, oxidation, and NMR characterization of a novel [60]fulleropyrrolidine containing a 15N isotope, showing an 85 ppm downfield heteroatom chemical shift. Preliminary details of the effects of substitution on the reactivity of the pyrrolidine ring are also reported.