Abstract
The bulk production of naphthyne derivatives of [60]fullerene, C 60, is achieved by pyrolysis of 1,8-diiodonaphthalene in the presence of C 60. Desorption chemical ionization mass spectra, recorded in the negative ion mode, show the addition of up to ten naphthyne units to a single C 60 molecule. Products containing two C 60 molecules are also generated. Tandem mass spectrometry confirms that covalent bonding has occurred. Similar reactions are described for the reactive intermediates generated from 1,8-naphthalic anhydride, 9-iodoanthracene, 2,6-dimethoxyiodobenzene, 2-iodonaphthalene and hexabromobenzene. Evidence for a [4 + 2] Diels—Alder ion/molecule reaction between mass-selected fullerene cations and methoxy-substituted 1,3-butadienes is presented. Ion/molecule reactions of various closed shell cations derived from the dissociative electron ionization of chlorine containing compounds are shown to result in the methylation, acylation, phenylation and benzylation of fullerenes in the course of positive ion chemical ionization. In the negative ion mode, halogenated fullerene anions are observed. At high desorption temperatures, the addition of at least 30 hydrogen atoms to C 60 is reported.
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