Biomedical subjects
Publications and source records attributed to GP Miller.
cis-Bisfullerene[60] adducts of 6,13-disubstituted pentacenes (R = Ph, 4'-hydroxymethylphenyl) are synthesized in 75% to 85% isolated yields under kinetically controlled Diels-Alder conditions. The cycloadditions are completely regioselective and highly stereoselective, with only traces of the diastereomeric trans-bisfullerene[60] adducts forming.
Experimental, molecular modeling, and model compound studies suggest that favorable fullerene[60] pi-stacking interactions in the ground state and in syn-transition states account for the high cis stereoselectivities observed in the reactions between C(60) and 6, 13-disubstituted pentacenes.
Thermal Diels-Alder reactions between C(60) and electron-deficient 3, 6-diaryl-1,2,4,5-tetrazines yield monoadducts possessing a diaryldihydropyridazine function nested atop the fullerene. The diaryldihydropyridazine functions direct a completely regioselective 1,4-hydrogenation, resulting in a racemic mixture of bifunctional bisadduct (+/-)-3.