FORMATION OF TETRABENZODISPIRO[4.0.4.3]TRIDECATETRAENE BY A TITANIUM-MEDIATED FLUORENYL COUPLING REACTION

被引:12
|
作者
FRITZE, C [1 ]
ERKER, G [1 ]
FROHLICH, R [1 ]
机构
[1] UNIV MUNSTER,INST ORGAN CHEM,D-48149 MUNSTER,GERMANY
关键词
TITANIUM; TETRABENZODISPIRO(4,3,4)TRIDECATEHAENE; COUPLING REACTION; METALLOCENES; CRYSTAL STRUCTURE;
D O I
10.1016/0022-328X(95)05588-G
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Treatment of 1,3-propanediol-ditosylate with fluorenyllithium yields 1,3-bis(fluorenyl)propane (5). Subsequent addition of methyllithium gives the corresponding dilithio compound 6. Dilithio-1,3-bis(fluorenyl)propane (6) was treated with titanium tetrachloride to yield the organic tetrabenzodispiro[4.0.4.3]tridecatetraene product 7, presumably formed by means of a carbon-carbon coupling reaction involving substituted fluorenyl radicals. The organic compounds 5 and 7 were identified by X-ray crystal structure analyses.
引用
收藏
页码:41 / 45
页数:5
相关论文
共 50 条
  • [41] Nickel-catalyzed cross-coupling between benzyl alcohols and alkenyl triflates assisted by titanium-mediated radical C-O bond cleavage
    Suga, Takuya
    Kondo, Miki
    Takahashi, Yuuki
    Ukaji, Yutaka
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2024, 97 (02)
  • [42] Luminogens for Aggregation-Induced Emission via Titanium-Mediated Double Nucleophilic Addition to 2,5-Dialkynylpyridines: Formation and Transformation of the Emitting Aggregates
    不详
    CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (19) : 4169 - 4169
  • [43] Titanium-mediated cross-coupling reactions of 1,3-butadiynes with α-iminonitriles to 3-aminopyrroles: observation of an imino aza-Nazarov cyclization
    You, Xu
    Xie, Xin
    Sun, Renhong
    Chen, Haoyi
    Li, Shi
    Liu, Yuanhong
    Organic Chemistry Frontiers, 2014, 1 (08): : 940 - 946
  • [44] Titanium-mediated diastereoselective formation of (Z)-1-(1-alkenyl)-2-substituted-cyclopropyl esters efficient precursors of (Z)-2,3-methanoamino acids
    Racouchot, S
    Ollivier, J
    Salaün, J
    SYNLETT, 2000, (12) : 1729 - 1732
  • [45] One-pot synthesis of polycyclic ring systems via titanium-mediated carbon-carbon bond formation. Activation of cyclopentadienyl ligand via irreversible reductive elimination
    Vu, AT
    Crowe, WE
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 212 : 11 - ORGN
  • [46] Regioselective carbon-carbon bond formation in titanium mediated reaction of ethylmagnesium bromide with allylic alcohols and allylic ethers
    Kulinkovich, OG
    Epstein, OL
    Isakov, VE
    Khmel'nitskaya, EA
    SYNLETT, 2001, (01) : 49 - 52
  • [47] Titanium-mediated formation of 1,2-disubstituted cyclopropanols from esters and alkenes. A new approach to the synthesis of 3,11-dimethylnonacosan-2-one, a sex pheromone of the German cockroach
    Epstein, OL
    Kulinkovich, OG
    TETRAHEDRON LETTERS, 1998, 39 (13) : 1823 - 1826
  • [48] Visible-Light-Mediated Vinyl-Thiophosphate Formation Via Three-Component Denitrative Cross-Coupling Reaction
    Huang, Xiao-Ying
    Zhu, Yu
    Ding, Zong-Cang
    Tang, Hai-Tao
    Pan, Ying-Ming
    Duan, Wen-Gui
    Cui, Fei-Hu
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (24) : 5015 - 5019
  • [49] Identification of unexpected unlabeled N,N-dimethylamide formation in the synthesis of deuterated fragment of ribociclib by a HATU-mediated coupling reaction
    Gai, Kuo
    Liu, Baomin
    Zhang, Yinsheng
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2019, 62 (02): : 62 - 66