title: Dramatic mechanistic change in acid-catalyzed arylation of azafulleroids depending on their ambident N/C basicity: formation of cyclopentene centered pentakisadduct.
abstract: Azafulleroid, amino-bridged [5,6]-open fullerene, has the ambident N/C basicity of the incorporated enamine moiety. Acid-catalyzed arylation of N-substituted azafulleroids proceeded via two types of initial N/C protonation to perform monoarylation or 1,4-bisarylation for the N-alkyl substituents and shuttlecock-type pentakisarylation for the N-phenyl substituent. The dramatic product change was explained by considering the possible mechanism as well as the DFT computational results.
authors.affiliation: Division of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-4593. ikuma@chem.eng.osaka-u.ac.jp.
authors.forename: Naohiko
authors.initials: N
authors.lastname: Ikuma
authors.forename: Yuta
authors.initials: Y
authors.lastname: Doi
authors.forename: Koichi
authors.initials: K
authors.lastname: Fujioka
authors.forename: Tsubasa
authors.initials: T
authors.lastname: Mikie
authors.forename: Ken
authors.initials: K
authors.lastname: Kokubo
authors.forename: Takumi
authors.initials: T
authors.lastname: Oshima
keywords: arylation; fullerenes; homogeneous catalysis; nucleophilic substitution; protonation