Syntheses of syn and anti doublebent [5]phenylene

被引:26
作者
Bong, DTY
Chan, EWL
Diercks, R
Dosa, PI
Haley, MM
Matzger, AJ
Miljanic, OS
Vollhardt, KPC [1 ]
Bond, AD
Teat, SJ
Stanger, A
机构
[1] Univ Calif Berkeley, Ctr New Direct Organ Synth, Dept Chem, Berkeley, CA 94720 USA
[2] Lawrence Berkeley Natl Lab, Div Chem Sci, Berkeley, CA 94720 USA
[3] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
[4] CCLRC, Daresbury Lab, Warrington WA4 4AD, Cheshire, England
[5] Technion Israel Inst Technol, Dept Chem, Inst Catalysis Sci & Technol, IL-32000 Haifa, Israel
[6] Technion Israel Inst Technol, Lise Meitner Minerva Ctr Computat Quantum Chem, IL-32000 Haifa, Israel
关键词
D O I
10.1021/ol049225v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The parent and dipropyl-substituted anti (1a,b) and syn doublebent (2a,b) [5]phenylenes have been assembled by CpCo-catalyzed double cyclization of regiospecifically constructed appropriate hexaynes. H-1 NMR, NICS, and an X-ray structural analysis of is reflect the aromatizing effect of double angular fusion on the central ring of the linear [3]phenylene substructure.
引用
收藏
页码:2249 / 2252
页数:4
相关论文
共 25 条
[1]   The heat of hydrogenation of (a) cyclohexatriene [J].
Beckhaus, HD ;
Faust, R ;
Matzger, AJ ;
Mohler, DL ;
Rogers, DW ;
Rüchardt, C ;
Sawhney, AK ;
Verevkin, SP ;
Vollhardt, KPC ;
Wolff, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (32) :7819-7820
[2]   A NEW APPROACH TO THE CONSTRUCTION OF BIPHENYLENES BY THE COBALT-CATALYZED COCYCLIZATION OF ORTHO-DIETHYNYLBENZENES WITH ALKYNES - APPLICATION TO AN ITERATIVE APPROACH TO [3]PHENYLENE, THE 1ST MEMBER OF A NOVEL CLASS OF BENZOCYCLOBUTADIENOID HYDROCARBONS [J].
BERRIS, BC ;
HOVAKEEMIAN, GH ;
LAI, YH ;
MESTDAGH, H ;
VOLLHARDT, KPC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (20) :5670-5687
[3]   2,3,9,10-TETRAKIS(TRIMETHYLSILYL)[5]PHENYLENE - SYNTHESIS VIA REGIOSPECIFIC COBALT-CATALYZED COCYCLIZATION OF 1,6-BIS(TRIISOPROPYLSILYL)-1,3,5-HEXATRIYNE [J].
BLANCO, L ;
HELSON, HE ;
HIRTHAMMER, M ;
MESTDAGH, H ;
SPYROUDIS, S ;
VOLLHARDT, KPC .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (12) :1246-1247
[4]   C-3-SYMMETRICAL HEXAKIS(TRIMETHYLSILYL)[7]PHENYLENE [TRIS(BIPHENYLENOCYCLOBUTADIENO)CYCLOHEXATRIENE], A POLYCYCLIC BENZENOID HYDROCARBON WITH SLIGHTLY CURVED TOPOLOGY [J].
BOESE, R ;
MATZGER, AJ ;
MOHLER, DL ;
VOLLHARDT, KPC .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (13-14) :1478-1481
[5]   Synthesis of bent [4]phenylene (cyclobuta[1,2-α:3,4-b′]bisbiphenylene) and structure of a bis(trimethylsilyl) derivative:: the last [4] phenylene isomer [J].
Bong, DTY ;
Gentric, L ;
Holmes, D ;
Matzger, AJ ;
Scherhag, F ;
Vollhardt, KPC .
CHEMICAL COMMUNICATIONS, 2002, (03) :278-279
[6]   En route to archimedene:: Total synthesis of C3h-symmetric [7]phenylene [J].
Bruns, D ;
Miura, H ;
Vollhardt, KPC ;
Stanger, A .
ORGANIC LETTERS, 2003, 5 (04) :549-552
[7]   Designer crystals: intermolecular interactions, network structures and supramolecular synthons [J].
Desiraju, GR .
CHEMICAL COMMUNICATIONS, 1997, (16) :1475-1482
[8]   NOVEL SYNTHESIS OF THE ANGULAR [3]PHENYLENE (TERPHENYLENE) BY COBALT-CATALYZED CYCLIZATION OF BIS(2-ETHYNYLPHENYL)ETHYNE - A MOLECULE WITH AN INTERNAL CYCLOHEXATRIENE RING [J].
DIERCKS, R ;
VOLLHARDT, KPC .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (03) :266-268
[9]   Cobalt-mediated synthesis of angular [4]phenylene: Structural characterization of a metal lacyclopentadiene(alkyne) intermediate and its thermal and photochemical conversion [J].
Dosa, PI ;
Whitener, GD ;
Vollhardt, KPC ;
Bond, AD ;
Teat, SJ .
ORGANIC LETTERS, 2002, 4 (12) :2075-2078
[10]  
Eickmeier C, 1999, ANGEW CHEM INT EDIT, V38, P800, DOI 10.1002/(SICI)1521-3773(19990315)38:6<800::AID-ANIE800>3.0.CO