Highly regioselective transformation of out/out-equatorial bis(formylmethano)[60]fullerenes: construction of dissymmetric [60]fullerene-centered triads.
Three kinds of out/out-equatorial bis(formylmethano)[60]fullerenes (1b-d) were obtained by the tether-directed bifunctionalization of [60]fullerene with bis(alpha-formylsulfonium ylide)s. The condensation of aromatic amines with 1b-d proceeded with an unexpectedly high regioselectivity to give one of two possible regioisomers of mono-imines as the main products (the ratio of the regioisomers, up to 97:3). By the transformation of the remaining formyl group in the mono-imines thus obtained, the corresponding dissymmetric bis-imines were efficiently synthesized.
Ito
Hiroshi
H
Department of Chemistry and Biotechnology, Graduate School of Engineering, University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-8656, Japan.
Ishida
Yasuhiro
Y
Saigo
Kazuhiko
K
D000588:Amines / Q000737:chemistry*; D001555:Benzene Derivatives / Q000138:chemical synthesis / Q000737:chemistry*; D002247:Carbon Isotopes; D004396:Coloring Agents / Q000737:chemistry; D037741:Fullerenes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008968:Molecular Conformation; D012680:Sensitivity and Specificity; D013237:Stereoisomerism
D000588:Amines; D001555:Benzene Derivatives; D002247:Carbon Isotopes; D004396:Coloring Agents; D037741:Fullerenes; C069837:fullerene C60