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. 2012 May 25;17(6):6395–6414. doi: 10.3390/molecules17066395

Table 2.

Acetalization of fullerene epoxide 1a with carbonyl compound in the presence of an acid catalyst.

graphic file with name molecules-17-06395-i003.jpg
Entry 2 Catalyst (equiv./amount) Reaction Time Yield a of 3 / %
1 graphic file with name molecules-17-06395-i004.jpg Inline graphic4a (0.29) 60 min 92
2 graphic file with name molecules-17-06395-i005.jpg Inline graphic4b (0.28) 90 min 91
3 graphic file with name molecules-17-06395-i006.jpg 4a (0.29) 60 min 95
4 graphic file with name molecules-17-06395-i007.jpg 4b (0.28) 4.5 h 88
5 graphic file with name molecules-17-06395-i008.jpg BF3·Et2O (one drop) 60 min 89
6 graphic file with name molecules-17-06395-i009.jpg Amberlyst 15® (268 mg/0.02 mmol) 3 h 96
7 graphic file with name molecules-17-06395-i010.jpg Montmorillonite (250 mg/0.02 mmol) 4 h reflux 60
8 graphic file with name molecules-17-06395-i011.jpg 4a (0.27) 30 min 45
9 R1=CH3, R2=C2H5 4a (0.27) 30 min 44
10 Cyclohexanone Amberlyst 15® (250 mg/0.02 mmol) 65 °C, 5 h in benzene 60
11 γ-Butyrolactone BF3·Et2O (one drop) 3 h in benzene 75

a Isolated yield.