Regioselective Synthesis and Crystallographic Characterization
of Isoxazoline-Ring-Fused Derivatives of Sc<sub>3</sub>N@<i>I</i><sub><i>h</i></sub>‑C<sub>80</sub> and C<sub>60</sub>
Highly regioselective
1,3-dipolar cycloaddition of 3,5-dichloro-2,4,6-trimethoxybenzonitrile
oxide (<b>1</b>) to Sc<sub>3</sub>N@<i>I</i><sub><i>h</i></sub>-C<sub>80</sub> or C<sub>60</sub> affords the corresponding
isoxazoline-ring-fused derivatives Sc<sub>3</sub>N@<i>I</i><sub><i>h</i></sub>-C<sub>80</sub>(C<sub>10</sub>H<sub>9</sub>O<sub>4</sub>NCl<sub>2</sub>) (<b>2a</b>) and C<sub>60</sub>(C<sub>10</sub>H<sub>9</sub>O<sub>4</sub>NCl<sub>2</sub>)
(<b>2b</b>). <b>2a</b> represents the first example of
an endohedral metallofullerene derivative with an isoxazoline ring.
Crystallographic and NMR spectroscopic studies reveal a [5,6]-bond
addition pattern in <b>2a</b> but a [6,6]-bond addition manner
in <b>2b</b>
