Efficient Regioselective [4+2] Cycloaddition of o-Quinodimethane to C70(CF3)10

被引：16
作者：
Takano, Yuta [1 ,2 ]
Angeles Herranz, M. [1 ]
Kareev, Ivan E. [3 ]
Strauss, Steven H. [4 ]
Boltalina, Olga V. [4 ]
Akasaka, Takeshi [2 ]
Martin, Nazario [1 ]
机构：
[1] Univ Tsukuba, Ctr Tsukuba Adv Res Alliance, Tsukuba, Ibaraki 3058577, Japan
[2] Univ Complutense, Fac Quim, Dept Quim Organ, E-28040 Madrid, Spain
[3] Russian Acad Sci, Inst Problems Chem Phys, Chernogolovka 142432, Russia
[4] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 17期
基金：
俄罗斯基础研究基金会;
关键词：
X-RAY; FULLERENE; C-60; SULTINES; C-76; DERIVATIVES; ADDUCTS; C-84; ESR; DFT;
D O I：
10.1021/jo9014358
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Diels-Alder reaction of C-1-C-70(CF3)(10) and 3,6-dimethoxy-1,2-quinodimethane leads regioselectively to the fort-nation of a new cycloadduct that has been fully characterized by spectroscopic and electrochemical methods as well its by X-ray diffraction.
引用
收藏
页码：6902 / 6905
页数：4
相关论文
共 34 条
  • [1] STRUCTURE AND PROPERTIES OF C70
    BAKER, J
    FOWLER, PW
    LAZZERETTI, P
    MALAGOLI, M
    ZANASI, R
    [J]. CHEMICAL PHYSICS LETTERS, 1991, 184 (1-3) : 182 - 186
  • [2] Thermal and microwave assisted reactions of 2,5-disubstituted thienosultines with [60]fullerene: non-Kekule biradicals and self-sensitized oxygenation of the cycloadduct
    Chi, CC
    Pai, IF
    Chung, WS
    [J]. TETRAHEDRON, 2004, 60 (48) : 10869 - 10876
  • [3] Thermal and microwave-assisted synthesis of Diels-Alder adducts of [60]fullerene with 2,3-pyrazinoquinodimethanes: Characterization and electrochemical properties
    FernandezPaniagua, UM
    Illescas, B
    Martin, N
    Seoane, C
    delaCruz, P
    delaHoz, A
    Langa, F
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (11) : 3705 - 3710
  • [4] Electrochemical, ESR and theoretical studies of [6,6]-opened C60(CF2), cis-2-C60(CF2)2 and their anions
    Goryunkov, Alexey A.
    Kornienko, Eugenia S.
    Magdesieva, Tatyana V.
    Kozlov, Andrey A.
    Vorobiev, Vsevolod A.
    Avdoshenko, Stanislav M.
    Ioffe, Ilya N.
    Nikitin, Oleg M.
    Markov, Vitality Yu.
    Khavrel, Pavel A.
    Vorobiev, Andrey Kh.
    Sidorov, Lev N.
    [J]. DALTON TRANSACTIONS, 2008, (48) : 6886 - 6893
  • [5] Thermally reversible C60-based donor-acceptor ensembles
    Herranz, MA
    Martín, N
    Ramey, J
    Guldi, DM
    [J]. CHEMICAL COMMUNICATIONS, 2002, (24) : 2968 - 2969
  • [6] 2,4-Bis(methylsulfanyl)pyrimidine o-quinodimethane: a versatile building block for functionalized fused pyrimidines
    Herrera, Antonio
    Martinez-Alvarez, Roberto
    Martin, Nazario
    Chioua, Mourad
    Chioua, Rachid
    Sanchez-Vazquez, Angel
    Molero, Dolores
    Almy, John
    [J]. TETRAHEDRON, 2009, 65 (08) : 1697 - 1703
  • [7] CHEMISTRY OF THE HIGHER FULLERENES - PREPARATIVE ISOLATION OF C-76 BY HPLC AND SYNTHESIS, SEPARATION, AND CHARACTERIZATION OF DIELS-ALDER MONOADDUCTS OF C-70 AND C-76
    HERRMANN, A
    DIEDERICH, F
    THILGEN, C
    TERMEER, HU
    MULLER, WH
    [J]. HELVETICA CHIMICA ACTA, 1994, 77 (07) : 1689 - 1706
  • [8] Synthesis of an asymmetric fullerene dimer via sequential cycloadditions
    Hingston, Timothy J.
    Sambrook, Mark R.
    Rees, Nicholas H.
    Porfyrakis, Kyriakos
    Briggs, G. Andrew D.
    [J]. TETRAHEDRON LETTERS, 2006, 47 (48) : 8595 - 8597
  • [9] A FACILE FORMATION OF ELECTROACTIVE FULLERENE ADDUCTS FROM SULTINES VIA A DIELS-ALDER REACTION
    ILLESCAS, B
    MARTIN, N
    SEOANE, C
    DELACRUZ, P
    LANGA, F
    WUDL, F
    [J]. TETRAHEDRON LETTERS, 1995, 36 (45) : 8307 - 8310
  • [10] Reaction of C-60 with sultines: Synthesis, electrochemistry, and theoretical calculations of organofullerene acceptors
    Illescas, BM
    Martin, N
    Seoane, C
    Orti, E
    Viruela, PM
    Viruela, R
    delaHoz, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22) : 7585 - 7591
1234