CHEMISTRY AT CYCLOPENTENE ADDENDS ON [60] FULLERENE - MATRIX-ASSISTEDLASER-DESORPTION IONIZATION TIME-OF-FLIGHT MASS-SPECTROMETRY (MALDI-TOF MS) AS A QUICK AND FACILE METHOD FOR THE CHARACTERIZATION OF FULLERENE DERIVATIVES

The reaction of Schwartz's reagent (1, (eta(5)-C5H5)(2)Zr(H)Cl), and N -bromo-succinimide or m-chloroperbenzoic acid with [60]fullerene leads to the formation of Diels-Alder products with bromo- and hydroxy-cycl opentadiene, respectively. A three-step mechanism to explain this unus ual reaction pathway is proposed. Epoxidation and hydrogenation of the double bond in the addend have been performed. Semi-empirical AMl cal culations are used to discuss the stereo-chemistry of the epoxides. Al l fullerene derivatives are characterized by matrix-assisted laser des orption-ionization time-of-flight mass spectrometry (MALDI-TOF MS). A routine method for the sample preparation is presented.