Abstract
Five kinds of 2,2-[60]fullerenoalkanals were synthesized by the fluoride ion-mediated reaction of [60]fullerene with 2-bromoenol silyl ethers, which were easily prepared by 2-bromination of the corresponding enol silyl ethers. The reactivity differed significantly depending on the stability of the 2-bromoenol silyl ethers. High yield and selectivity were achieved for the reaction of 2-bromoenol trimethylsilyl ethers under mild conditions (KF/18-crown-6-ether). The reaction of stable 2-bromoenol tert-butyldimethylsilyl ethers, on the other hand, required the use of more reactive tetrabutylammonium fluoride as a fluoride ion source.
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