Reactions of [60]Fullerene with Halides and Amino Acids to Synthesize Fulleropyrrolidines

Abstract

AbstractThe reactions of [60]fullerene with benzyl chlorides and amino acids in chlorobenzene (PhCl) were investigated. Fulleropyrrolidines bearing ArCH moieties originating from the corresponding benzyl chlorides through C–Cl bond cleavage were obtained from these reactions. Use of PhCl/DMSO instead of PhCl as the solvent significantly improved the reaction efficiency. A detailed investigation of these reactions resulted in the discovery of other halides – such as allyl chloride, methallyl chloride, cinnamyl chloride, propargyl bromide, ethyl bromoacetate, bromoacetonitrile, bromomethane, bromopropane and bromobutane – that could also react with [60]fullerene and amino acids to produce fulleropyrrolidines. This reaction could be an alternative to the Prato reaction for synthesizing fulleropyrrolidines when aldehydes are expensive or unavailable from commercial sources. A plausible reaction mechanism for product formation involving C–X bond cleavage in the halide to form the aldehyde is proposed.