Issue 29, 2016
From the journal:

Organic & Biomolecular Chemistry

Regioselective addition of Grignard reagents to tosylazafulleroid and derivatization to 1,2-disubstituted [60]fullerene†

Naohiko Ikuma,*a   Koji Nakagawa,a   Ken Kokuboa  and  Takumi Oshimaa  

* Corresponding authors

a Division of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
E-mail: ikuma@chem.eng.osaka-u.ac.jp

Abstract

Grignard reagents (RMgBr: R = Et, p-tolyl) selectively attacked the β-position of the bridgehead double bond of tosylazafulleroid through interaction of Mg with the S[double bond, length as m-dash]O group. The following [5,6] ring closure and C–N bond scission led to aryl/alkyl aminylfullerenes with 1,2-configuration. Tolyl-substituted aminylfullerene was further converted into 1,4-di(p-tolyl)fullerene on treatment in acidic toluene.

Graphical abstract: Regioselective addition of Grignard reagents to tosylazafulleroid and derivatization to 1,2-disubstituted [60]fullerene

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Article information

DOI
https://doi.org/10.1039/C6OB00869K
Article type
Paper
Submitted
22 Apr 2016
Accepted
29 Jun 2016
First published
29 Jun 2016
This article is Open Access
Creative Commons BY-NC license

Org. Biomol. Chem., 2016,14, 7103-7108

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Regioselective addition of Grignard reagents to tosylazafulleroid and derivatization to 1,2-disubstituted [60]fullerene

N. Ikuma, K. Nakagawa, K. Kokubo and T. Oshima, Org. Biomol. Chem., 2016, 14, 7103 DOI: 10.1039/C6OB00869K

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