946 J. Am. Chem. Soc., Vol. 119, No. 5, 1997
BellaVia-Lund and Wudl
681 (w), 678 (w), 675 (m), 644 (w), 589 (m), 571 (w), 559 (w), 543
2H), 3.35 (s, 3H) ppm; 13C NMR (CS2/D2O, 125 MHz) 154.2, 150.0,
149.6, 149.5, 149.2, 149.1, 148.7, 147.6, 147.58, 147.4, 147.35, 147.2,
147.1, 147.0, 146.9, 146.8, 146.7, 146.5, 146.4, 146.3, 146.26, 146.2,
145.7, 145.6, 145.2, 144.9, 144.0, 143.5, 143.4, 143.2, 143.1, 143.0,
142.6, 142.5, 142.3, 142.1, 141.7, 141.5, 140.7, 140.3, 139.9, 139.3,
138.6, 135.5, 134.5, 134.4, 134.3, 132.6, 130.9, 130.0, 129.6, 129.2,
128.8, 128.0, 127.6, 127.3, 126.7, 126.6, 125.5, 124.4, 123.2, 121.5,
82.7, 71.3, 67.3, 57.8 ppm; -FAB-MS (chloroform/NBA) m/z 943-
(m)+, 840 (C70)+. [6,6]-(1-N-MEM-fulleroaziridine)-C70 7: UV/vis
(toluene) λmax 450, 376, 316, 288 nm; IR (DRIFT) 2959 (m), 2920
(m), 2893 (m), 1462 (s), 1386 (w), 1156 (s), 1119 (m), 1092 (w), 1015
(w), 803 (m), 687 (w), 680 (w), 672 (m), 651 (m), 586 (m), 564 (w),
1
(w), 538 (m), 453 (w) cm-1; H NMR (CS2/D2O, 500 MHz) 4.76 (s,
2H), 4.16 (t, J ) 4.8 Hz, 2H), 3.68 (t, J ) 4.8 Hz, 2H), 3.40 (s, 3H)
ppm; 13C NMR (CS2/D2O, 125 MHz): 153.9, 150.8 (1C), 150.7, 150.7,
150.1, 150.1, 148.9, 148.6, 148.6, 148.1, 148.0, 147.9, 147.5, 147.5,
147.1, 147.0, 146.6, 145.8 (1C), 145.6, 145.3, 143.7, 143.6, 143.4,
143.4, 143.0, 142.7, 142.2, 141.8, 140.9, 136.8, 132.9, 131.9, 130.5,
130.5, 130.4, 130.2, 127.2, 82.3, 79.7 (bridgehead C), 79.6 (bridgehead
C), 72.1, 69.2, 58.6 ppm; -FAB-MS (chloroform/NBA), m/z 943 (M)+,
841 (C70)+. [5,6]-(1-N-MEM-azafulleroid)-C70 5: UV/vis (toluene)
λmax 468, 392, 336, 288 nm; IR (DRIFT) 2969 (m), 2928 (m), 2889
(w), 1598 (w), 1578 (w), 1426 (m), 1446 (s), 1325 (w), 1244 (w), 1125
(s), 816 (m), 687 (m), 583 (m),554 (m), 504 (m) cm-1; 1H NMR (CS2/
D2O, 500 MHz) 5.27 (s, 2H), 4.29 (t, J ) 4.8 Hz, 2H), 3.77 (t, J ) 4.8
Hz, 2H), 3.45 (s, 3H) ppm; 13C NMR (CS2/D2O, 125 MHz) 151.8,
150.4, 149.8, 148.5, 148.3 (1C), 148.0, 147.8, 147.7, 147.5, 147.2,
147.0, 146.8, 146.0, 145.7, 144.8, 144.3, 144.1, 144.0, 143.9, 143.5,
143.3, 143.2, 142.7, 141.6, 139.6, 139.5, 136.5 (1C), 135.3, 134.8 (1C),
132.2, 132.2, 131.2, 130.9, 128.1, 128.0 (1C), 127.9, 84.8, 72.2, 68.4,
58.6 ppm; -FAB-MS (chloroform/NBA) m/z 943 (M)+, 840 (C70)+.
[5,6]-(1-N-MEM-azafulleroid)-C70 6: UV/vis (toluene) λmax 468, 384,
340, 286 nm; IR (DRIFT) 2945 (m), 2890 (m), 1557 (w), 1442 (s),
1397 (w), 1108 (m), 809 (w), 688 (m), 650 (w), 631 (m), 581 (m), 561
(m), 531 (w), 459 (m) cm-1; 1H NMR (CS2/D2O, 500 MHz) 4.95 (2H,
AB, δA ) 4.97, δB ) 4.92, JAB ) 9.5 Hz), 4.02 (2H; dt, AB(M2), δA)
4.02, δB ) 4.01, JAB ) 2 Hz, JAM ) JBM ) 5 Hz), 3.61 (t, J ) 5 Hz,
1
529 (w), 456 (w) cm-1; H NMR (CS2/D2O, 500 MHz) 4.69 (s, 2H),
4.11 (t, J ) 4.6 Hz, 2H), 3.70 (t, J ) 4.6 Hz, 2H), 3.44 (s, 3H) ppm;
13C NMR (CS2/D2O, 125 MHz) 151.9 (1C), 150.8, 149.4, 149.1 (1C),
148.5, 148.4, 148.2, 147.9, 147.8, 147.7, 147.1, 146.92 (1C), 146.86,
146.6, 146.6, 145.7, 145.5, 145.1, 144.6, 144.3, 144.1, 143.4, 142.2
(1C), 131.7, 131.4, 131.4, 130.8, 82.7, 73.5 (bridgehead C), 71.9, 69.0,
58.5 ppm; -FAB-MS (chloroform/NBA), m/z 943 (M)+, 840 (C70)+.
Acknowledgment. We thank the National Science Founda-
tion for support through the MRSEC and Grants DMR-9122536
and DMR-9500888.
JA963063J