High Quality Content by WIKIPEDIA articles! The Prato reaction in fullerene chemistry describes the functionalization of fullerenes and nanotubes with azomethine ylides in a 1,3-dipolar cycloaddition. The amino acid sarcosine reacts with paraformaldehyde when heated at reflux in toluene to an ylide which reacts with a double in a 6,6 ring position in a fullerene in a 1,3-dipolar cycloaddition to yield a N-methylpyrrolidine derivative or pyrrolidinofullerene or pyrrolidino[[3,4:1,2]] [60]fullerene in 82% yield. In one application a liquid fullerene is obtained when the pyrrolidone substituent is a 2,4,6-tris(alkyloxy)phenyl group although a small amount of solvent is still required. This method is also used in the functionalization of single wall nanotubes. When the amino acid is modified with a glycine chain the resulting nanotubes are soluble in common solvents such chloroform and acetone. Another characteristic of the treated nanotubes is their larger aggregate dimensions compared to untreated nanotubes.

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