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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