Regioselective thermal cage-opening reactions of 4-amino substituted 1,3-bishomocubanones

被引:6
作者
Bakkeren, FJAD [1 ]
Schröer, F [1 ]
Klunder, AJH [1 ]
Zwanenburg, B [1 ]
机构
[1] Catholic Univ Nijmegen, Dept Organ Chem, NSR Mol Struct Design Design & Synth, NL-6525 ED Nijmegen, Netherlands
关键词
D O I
10.1016/S0040-4039(98)02116-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Thermolysis of 4-substituted 1,3-bishomocubanones is strongly dependent on the electronic nature of the bridgehead substituent. 4-(N-benzyl)amido-substituted cage compounds 12 unexpectedly furnish bicyclic annelated cyclopentenones 13, whereas the 4-acetoxy-1,3-bishomocubanone is thermally stable up to 750 degrees C. The free benzylamine 16 undergoes cage opening even at room temperature to give tetracyclic dione 17. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:9531 / 9534
页数:4
相关论文
共 18 条
  • [1] Unusual photochemical behavior of 5-amino-endo-dicyclopentadien-3-ones
    Bakkeren, FJAD
    Schröer, F
    de Gelder, R
    Klunder, AJH
    Zwanenburg, B
    [J]. TETRAHEDRON LETTERS, 1998, 39 (51) : 9527 - 9530
  • [2] REARRANGEMENTS OF OXO-DICYCLOPENTADIENES
    COOKSON, RC
    HUDEC, J
    WILLIAMS, RO
    [J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (15): : 1382 - &
  • [3] DEMEIJERE A, 1989, STRAIN ITS IMPLICATI
  • [4] CUBANES - STARTING MATERIALS FOR THE CHEMISTRY OF THE 1990S AND THE NEW CENTURY
    EATON, PE
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (11): : 1421 - 1436
  • [5] EATON PE, 1986, TETRAHEDRON, V42, P1549
  • [6] GEENBERG A, 1978, STRAINED ORGANIC MOL, V38
  • [7] HALTON B, 1992, ADV STRAIN ORGANIC C, V2
  • [8] CONTROL OF CAGE OPENING REACTIONS IN THE 1,3-BISHOMOCUBANE AND HOMOCUBANE SYSTEMS
    KLUNDER, AJH
    ARIAANS, GJA
    VANDERLOOP, EARM
    ZWANENBURG, B
    [J]. TETRAHEDRON, 1986, 42 (06) : 1903 - 1915
  • [9] STRAINED BRIDGEHEAD CAGE ALCOHOLS AND DERIVATIVES
    KLUNDER, AJH
    ZWANENBURG, B
    [J]. CHEMICAL REVIEWS, 1989, 89 (05) : 1035 - 1050
  • [10] NUCLEOPHILIC ELIMINATIVE RING FISSION OF BRIDGEHEAD SUBSTITUTED 1,3-BISHOMOCUBYL ACETATES
    KLUNDER, AJH
    DEVALK, WCGM
    VERLAAK, JMJ
    SCHELLEKENS, JWM
    NOORDIK, JH
    PARTHASARATHI, V
    ZWANENBURG, B
    [J]. TETRAHEDRON, 1985, 41 (05) : 963 - 973