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O
O
Ball milling
O
Ball milling
C
60
O or C
60
Ball milling
decomposition
O
(C
60
O)
n
Oxide polymer
C
60
+
O
Scheme 1.52 Mechanochemical oxygenation of fullerene.
R
N
N
HSBM, 30 min.
N
+
R-N
3
H
44
CPh
3
R
=
a
62-76%
b
R
N
N
R
Solid state
120 °C, 2 h
44b
+
Scheme 1.53 Mechanochemical [2
þ
3] cycloaddition reaction of fullerene and or-
ganic azide.
triazoline derivative was heated at 120 1C for 2 h in the solid state, the
corresponding 5,6-open and 6,6-closed aza fullerenes were obtained
(Scheme 1.53).
Mechanochemical [2
þ
3] cycloaddition reaction of fullerene with diazo
compound gives the corresponding C
60
-fused-2-pyrazoline 46 within 30 min.
2-Pyrazoline 46 was obtained via isomerization of 1-pyrazoline 45, which was
formed directly by the 1,3-dipolar cycloaddition of C
60
with ethyl diazoace-
tate generated in situ from the glycine ester hydrochloride and NaNO
2
(Scheme 1.54).
50
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