title: Highly regioselective synthesis of bis-aziridino[60]fullerene with sulfilimine.
abstract: In the course of our study of the development of a synthetic methodology for the aziridination of fullerenes, we recently reported the photochemical [2+1] cycloaddition reaction of nitrene onto C(60) generated from sulfilimine. Sulfilimines with an electron-donating group on the N atom are well known to undergo Michael-type reactions, followed by concomitant elimination of sulfide to afford the corresponding aziridines. In these reactions, sulfilimines act as a nucleophile to the electrophilic olefins. Furthermore, C(60) has characteristic features of a low LUMO level and electron-accepting properties. Therefore, it can be an electrophilic olefin. In this context, sulfilimines might react with C(60) to afford the corresponding aziridinofullerenes. We have studied the thermal reaction of (S,S)-diphenylsulfilimines with C(60) and regioselectively synthesized bis- and tris-aziridinated fullerenes. These structures were determined through spectroscopic analyses. Among these, the structure of bis-aziridinated[60]fullerene, C(60)(NCH(3))(2), was determined using single-crystal X-ray analysis. Results show that the multi-aziridination occurs exclusively at the same six-membered ring of C(60) to afford one isomer of the bis-adduct and tris-adduct.
authors: Center for Tsukuba Advanced Research Alliance, University of Tsukuba, Tsukuba, Ibaraki 305-8577, Japan.
authors: Mitsunori
authors: M
authors: Okada
authors: Tsukasa
authors: T
authors: Nakahodo
authors: Midori O
authors: MO
authors: Ishitsuka
authors: Hidefumi
authors: H
authors: Nikawa
authors: Takahiro
authors: T
authors: Tsuchiya
authors: Takeshi
authors: T
authors: Akasaka
authors: Tetsuo
authors: T
authors: Fujie
authors: Toshiaki
authors: T
authors: Yoshimura
authors: Zdenek
authors: Z
authors: Slanina
authors: Shigeru
authors: S
authors: Nagase