Ring-opening reaction of cyclopropanated [60]fullerenes: unexpected transformation of methano[60]fullerenes having an electron-donating group on the methano-bridge carbon.
A series of novel transformations of [60]fullerene derivatives were found, starting from methano[60]fullerenes with an electron-donating group on the methano-bridge carbon. Aminomethano[60]fullerenes, in situ generated by the treatment of their trifluoromethanesulfonic acid salts with a base, were readily converted into 1-acyl-1,2-dihydro[60]fullerenes via the ring opening of the cyclopropane moiety. The aldehyde/ketones thus obtained were easily hydrolyzed to give 1,2-dihydro[60]fullerene in the presence of hydroxide anions.
Tada
Tomoyuki
T
Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-8656, Japan.
Ishida
Yasuhiro
Y
Saigo
Kazuhiko
K