A SIMPLE ROUTE TO SULFUR-BRIDGED ANNULENES

被引:99
作者
HU, ZY [1 ]
ATWOOD, JL [1 ]
CAVA, MP [1 ]
机构
[1] UNIV ALABAMA,DEPT CHEM,TUSCALOOSA,AL 35487
关键词
D O I
10.1021/jo00105a025
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The McMurry coupling reaction of thiophene-derived dialdehydes has been employed as the key step in the synthesis of the sulfur-bridged annulenes 3, 4, 6-9, and 14. Dication 9 is the second example of a peripherally aromatic (26 pi) dication of this class, while the 22 pi annulene 14 is the first neutral aromatic annulene derived solely from thiophene.
引用
收藏
页码:8071 / 8075
页数:5
相关论文
共 33 条
  • [1] PREPARATION AND PROPERTIES OF THIOPHEN ANALOGUES OF PORPHYRINS AND RELATED SYSTEMS .3.
    AHMED, M
    METHCOHN, O
    [J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (11): : 2104 - &
  • [2] BADGER GM, 1964, P CHEM SOC LONDON, P82
  • [3] SYNTHESIS OF [18]ANNULENE TRISULPHIDE
    BADGER, GM
    ELIX, JA
    LEWIS, GE
    [J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1965, 18 (01) : 70 - &
  • [4] SYNTHESIS OF 22 PI-ELECTRON MACROCYCLES - SAPPHYRINS AND RELATED COMPOUNDS
    BROADHURST, MJ
    JOHNSON, AW
    GRIGG, R
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1972, (16): : 2111 - +
  • [5] SYNTHESIS OF PORPHIN ANALOGUES CONTAINING FURAN AND/OR THIOPHEN RINGS
    BROADHURST, MJ
    JOHNSON, AW
    GRIGG, R
    [J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (21): : 3681 - +
  • [6] COULSON CA, 1964, P CHEM SOC LONDON, P220
  • [7] SYNTHESIS AND PARATROPICITY OF HETEROATOM-BRIDGED [17]ANNULENONES
    CRESP, TM
    SARGENT, MV
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (23): : 2961 - 2971
  • [8] DEMUNNO G, 1993, TETRAHEDRON, V49, P6863
  • [9] BRIDGED [18]ANNULENES - STUDY OF SYNTHESIS AND PROPERTIES OF C-12, 12D, 12E, 12F-TETRAHYDROBENZO[G,H,I]PERYLENE AND ITS ANALOGS
    DUVERNET, RB
    WENNERSTROM, O
    LAWSON, J
    OTSUBO, T
    BOEKELHEIDE, V
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (08) : 2457 - 2464
  • [10] THE TETRATHIAPORPHYCENE REDOX SYSTEM - ELECTROCHEMICAL REDUCTION OF A 20-PI CYCLOPHANE TO ITS DIATROPIC 22-PI DIANION
    ELLINGER, F
    GIEREN, A
    HUBNER, T
    LEX, J
    LUCCHESINI, F
    MERZ, A
    NEIDLEIN, R
    SALBECK, J
    [J]. MONATSHEFTE FUR CHEMIE, 1993, 124 (8-9): : 931 - 943