Unexpected fullerene dimerization via [5,6]-bond upon functionalization of Cs-C70(CF3)8 by the Bingel reaction

被引：16

作者：

Ovchinnikova, Natalia S. ^{[1
]}

Goryunkov, Alexey A. ^{[1
]}

Khavrel, Pavel A. ^{[1
]}

Belov, Nikita M. ^{[1
]}

Apenova, Marina G. ^{[1
]}

Ioffe, Ilya N. ^{[1
]}

Yurovskaya, Marina A. ^{[1
]}

Troyanov, Sergey I. ^{[1
]}

Sidorov, Lev N. ^{[1
]}

Kemnitz, Erhard ^{[2
]}

机构：

[1] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119991, Russia

[2] Humboldt Univ, Inst Chem, D-12489 Berlin, Germany

来源：

DALTON TRANSACTIONS | 2011年 / 40卷 / 04期

基金：

俄罗斯基础研究基金会;

关键词：

ISOMERS; CRYSTAL;

D O I：

10.1039/c0dt00777c

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The Bingel reaction of the C-s isomer of C-70(CF3)(8) has been found to yield two C-70(CF3)(8)[C(CO2Et)(2)] monoadducts and one C-70(CF3)(8)[C(CO2Et)(2)](2) bisadduct as its major products. Malonate addition occurs at those [6,6]-bonds that radiate from the polar pentagons of the C-70(CF3)(8) cage. Unexpectedly, X-ray single crystal analysis reveals dimerization of the above substances during crystallization, providing two isomers of {C-70(CF3)(8)[C(CO2Et)(2)]}(2), one isomer of {C-70(CF3)(8)[C(CO2Et)(2)](2)}(2) and {C-70(CF3)(8)}(2). This dimerization represents [2+2]-cycloaddition via [5,6]-bonds and results in functionalization patterns resembling several known C70X10 derivatives.

引用

页码：959 / 965

页数：7

共 12 条

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[2] Reductive Hydrogenation of Cs-C70(CF3)8 and C1-C70(CF3)10
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[3] Regioselective near-equatorial chlorination of Cs-C70(CF3)8
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Sidorov, Lev N.
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[5] Kinetically Controlled Near-Equatorial Alkylation of Cs-C70(CF3)8 Dianions
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ELECTROCHIMICA ACTA, 2025, 524
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[8] Synthesis of the first dihydrofuran derivative of fullerene C70, 4′-acetyl-5′-methylfurano[2′,3′:7,8]-(C70-D5h(6))[5,6]fullerene by Reaction of C70 with VO(acac)2, MoO2(acac)2, and Ni(acac)2
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Russian Journal of Organic Chemistry, 2013, 49 : 1842 - 1844
[9] Synthesis of the first dihydrofuran derivative of fullerene C70, 4′-acetyl-5′-methylfurano[2′,3′:7,8]-(C70-D 5h(6))[5,6]fullerene by Reaction of C70 with VO(acac)2, MoO2(acac)2, and Ni(acac)2
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[10] Nitrogen Directs Multiple Radical Additions to the 9,9′-Bi-1-aza(C60-Ih)[5,6]fullerene: X-ray Structure of 6,9,12,15,18-C59N(CF3)5
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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (24) : 5537 - 5540

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