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A nanosecond time-resolved resonance Raman (ns-TR3) spectroscopic study of the reactions of the 2-fluorenylnitrenium ion with several C8-substituted guanosine derivatives is reported. The TR3 spectra show that the 2-fluorenylnitrenium ion reacts with the C8-substituted guanosine derivatives (C8-methylguanosine and C8-bromoguanosine) to produce C8 intermediates with the methyl and bromine moieties still attached to the intermediate species at the C8 position. The C8-bromoguanosine species was observed to be less reactive toward the 2-fluorenylnitrenium ion compared to the guanosine and C8-methylguanosine species. Comparison of the TR3 spectra to the results obtained from density functional theory calculations was used to characterize the C8 intermediates observed to learn more about their structure and properties. The implications of these results for the chemical reactivity of arylnitrenium ions toward substituted guanosine derivatives are briefly discussed.

A multipolymer reaction system has been developed in which a water-soluble polymer-supported 2,2'-bipyridine group and a similarly immobilized TEMPO derivative are used as ligands for copper to effect the mild and selective aerobic oxidation of primary alcohols in acetonitrile-water solvent. In this reaction system, poly(ethylene glycol) monomethyl ether (molecular weight = 5000 Da) was used as the support for both the 2,2'-bipyridine and TEMPO moieties because of its solubility properties. The use of these functionalized polymers simultaneously in catalytic quantities allows for primary alcohols to be oxidized selectively to the corresponding aldehydes in an environmentally friendly manner. This is the first reported example of using two different polymer-supported ligands together to form an organometallic species capable of catalyzing an organic reaction.

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