Diels-Alder reactivity of 2-(bromomethyl)-1,4-quinone and 2-bromo-5-(bromomethyl)-1,4-quinone with cyclopentadiene and the synthesis of new substituted pentacyclic systems

被引:5
作者
Sudhir, U [1 ]
James, B [1 ]
Joly, S [1 ]
Nair, MS [1 ]
机构
[1] CSIR, Reg Res Lab, Div Organ Chem, Trivandrum 695019, Kerala, India
关键词
Diels-Alder reactivity; bromomethylquinones; polycyclic cage compounds; C-13-NMR;
D O I
10.1163/156856703322149053
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Photochemical synthesis of the novel compounds 3-bromotetracyclo [5.3.1.0(2,6).0(4.8)] undec-10(12)-ene-9,11-dione, 1-(bromomethyl)pentacyclo [5.4.0.0(2,6).0(3.10).0(5,9)]undeca-8,11-dione and 1-bromo-9-(bromomethyl)pentacyclo [5.4.0.0(2,6).0(3,10).0(5.9)]undeca-8,11-dione is described.
引用
收藏
页码:523 / 532
页数:10
相关论文
共 16 条
  • [1] Nucleophilic additions of primary and secondary amines to pentacyclo[5.4,0.0(2,6).0(3,10).0(5,9)]undecane-8,11-dione
    Bott, SG
    Marchand, AP
    Kumar, KA
    Vidyanand, D
    Xing, DX
    Watson, WH
    Kashyap, RP
    Sachleben, RA
    [J]. JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 1995, 25 (10) : 633 - 640
  • [2] PHOTOCHEMICAL CYCLISATION OF DIELS-ALDER ADDUCTS
    COOKSON, RC
    CRUNDWELL, E
    HILL, RR
    HUDEC, J
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1964, (SEP): : 3062 - &
  • [3] MACHAND AP, 1992, TETRAHEDRON LETT, V33, P3983
  • [4] Marchand A. P., 1989, ADV THEORETICALLY IN, V1, P357
  • [5] Marchand AP, 1998, TETRAHEDRON, V54, P15105, DOI 10.1016/S0040-4020(98)00909-0
  • [6] SYNTHESIS AND CHEMISTRY OF A NEW, FUNCTIONALIZED POLYCYCLIC AZOALKANE - A NOVEL ENTRY INTO THE HOMOPENTAPRISMANE RING-SYSTEM
    MARCHAND, AP
    REDDY, GM
    WATSON, WH
    KASHYAP, RP
    NAGL, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (01) : 277 - 282
  • [7] REDUCTIVE AMINATION OF PENTACYCLO[5.4.0.0/2,6/0/3,10/0/5,9]UNDECANE-8,11-DIONE
    MARCHAND, AP
    DAVE, PR
    SATYANARAYANA, N
    ARNEY, BE
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (05) : 1088 - 1092
  • [8] Marchand AP, 1995, ALDRICHIM ACTA, V28, P95
  • [9] TRANS-ANNULAR CYCLIZATIONS IN THE PENTACYCLO[5.4.0.02,6.03,10.05,9]UNDECANE-8,11-DIONE SYSTEM - A REINVESTIGATION
    MARCHAND, AP
    ARNEY, BE
    DAVE, PR
    SATYANARAYANA, N
    WATSON, WH
    NAGL, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (11) : 2644 - 2647
  • [10] TOTAL SYNTHESIS OF THE MARINE NATURAL PRODUCT (+/-)-PRECAPNELLADIENE
    MEHTA, G
    MURTY, AN
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (16) : 1058 - 1060