Reactions of Iminoglycines with C60 Fullerene and their Unambiguous Characterisation using NMR Spectroscopy

Authors

Paul A. Keller, University of WollongongFollow
Stephen G. Pyne, University of WollongongFollow
Bill C. Hawkins, University of Wollongong

RIS ID

16739

Publication Details

This article was originally published as: Keller, PA, Pyne, SG & Hawkins, BC, Reactions of Iminoglycines with C60 Fullerene and their Unambiguous Characterisation using NMR Spectroscopy, Comptes Rendus Chimie, 2006, 9(7-8), 1100-1106. The original journal can be found here through Elsevier.

Abstract

This review examines the addition of iminoglycine derivatives to C60, yielding protected fullerenyl pyrroline derivatives. Subsequent reduction with sodium cyanoborohydride produces ring-opening adducts which are protected fullerenyl α-amino acids. Pyrroline bisadducts can be produced using tethers to link two iminoglycine units together, and variations include combining with malonate reactive groups this giving rise to interesting observations as to the regioselectivity of such reactions. All derivatives are fully characterised by NMR spectroscopy, and in the case of bis-adducts, the regioselectivity is determined from 1H/13C and 13C/13C connectivity patterns using HMBC and INADEQUATE experiments, respectively, thus eliminating the need for comparative techniques or X-ray crystallography to determine the structures.