메뉴 건너뛰기




Volumn 2, Issue 1, 1996, Pages 58-67

Centropentaindan, a fenestrane bearing five mutually fused indan units: Syntheses, molecular structure, and bridgehead substitution

Author keywords

Centropolyindans; Cyclodehydrogenation; Fenestranes; Polycycles; Triquinacenes

Indexed keywords

CENTROPOLYINDANS; CYCLODEHYDROGENATION; FENESTRANES; POLYCYCLES; TRIQUINACENES;

EID: 0001900211     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.19960020112     Document Type: Article
Times cited : (26)

References (77)
  • 17
    • 84989487596 scopus 로고
    • k) D. Kuck, ibid. 1994, 127, 409-425.
    • (1994) Chem. Ber. , vol.127 , pp. 409-425
    • Kuck, D.1
  • 30
    • 84891433771 scopus 로고
    • Ph. D Thesis, Harvard University
    • b) H. E. Simmons III, Ph. D Thesis, Harvard University, 1980.
    • (1980)
    • Simmons III, H.E.1
  • 31
    • 84891458494 scopus 로고    scopus 로고
    • A derivative of tribenzocentropentaquinane was obtained and fully characterized (cf. ref. [4 g])
    • A derivative of tribenzocentropentaquinane was obtained and fully characterized (cf. ref. [4 g]).
  • 35
    • 84891426755 scopus 로고
    • Doctoral Thesis, University of Bielefeld
    • R. A. Krause, Doctoral Thesis, University of Bielefeld, 1992.
    • (1992)
    • Krause, R.A.1
  • 47
    • 84891420064 scopus 로고
    • Doctoral Thesis, University of Bielefeld
    • A. Schuster, Doctoral Thesis, University of Bielefeld, 1991.
    • (1991)
    • Schuster, A.1
  • 48
    • 84891377900 scopus 로고
    • Inspection of molecular models suggests that only the sixth bromine atom should cause a particularly strong 1,3-interaction, in accord with the experimental evidence that a pentabromo derivative of 8 is formed predominantly with a large excess of bromine reagent; Doctoral Thesis, University of Bielefeld
    • Inspection of molecular models suggests that only the sixth bromine atom should cause a particularly strong 1,3-interaction, in accord with the experimental evidence that a pentabromo derivative of 8 is formed predominantly with a large excess of bromine reagent; D. Gestmann, Doctoral Thesis, University of Bielefeld, 1994.
    • (1994)
    • Gestmann, D.1
  • 49
    • 84891398605 scopus 로고    scopus 로고
    • note
    • 13C chemical shifts of the central carbon nuclei increase almost linearly with the increasing number of o-phenylene bridges.
  • 50
    • 84891468048 scopus 로고    scopus 로고
    • note
    • Centropolyindans with a conformationally flexible molecular framework, such as fenestrindan 10a, exhibit a slight hypsochromic shift of the α band (Δδ≈-2.5 nm).
  • 51
    • 84891406893 scopus 로고    scopus 로고
    • X-ray crystal structure analyses of 10b and 10d have been performed: to be published
    • a) X-ray crystal structure analyses of 10b and 10d have been performed: D. Kuck, A. Schuster, W. Saak, S. Pohl, to be published;
    • Kuck, D.1    Schuster, A.2    Saak, W.3    Pohl, S.4
  • 52
    • 84891421797 scopus 로고    scopus 로고
    • note
    • b) The measurements gave α = 121.4° and β = 34.4° for 10b and α = 118.6° and β = 35.6° for 10d.
  • 56
    • 84891462780 scopus 로고    scopus 로고
    • 2v symmetrical structure
    • 2v symmetrical structure.
  • 59
    • 0004320505 scopus 로고
    • MM + in the software package Hypercube, Waterloo, Ontario
    • c) MM + in the software package HyperChem 4.0, Hypercube, Waterloo, Ontario, 1994.
    • (1994) HyperChem 4.0
  • 61
    • 0001231365 scopus 로고
    • X-ray structural analysis of triquinacene
    • b) X-ray structural analysis of triquinacene: E. D. Stevens, J. D. Kramer, L. A. Paquette, J. Org. Chem. 1976, 41, 2266-2269.
    • (1976) J. Org. Chem. , vol.41 , pp. 2266-2269
    • Stevens, E.D.1    Kramer, J.D.2    Paquette, L.A.3
  • 64
    • 84891374586 scopus 로고    scopus 로고
    • For 1, the MM + force field suggests α = C(8b)-C(16d)-C(16b) = 113.8° and |β| < 0.2° (cf. exp. values in Table 1)
    • a) For 1, the MM + force field suggests α = C(8b)-C(16d)-C(16b) = 113.8° and |β| < 0.2° (cf. exp. values in Table 1).
  • 65
    • 84891406887 scopus 로고    scopus 로고
    • According to our experience, MM calculations systematically underestimate the flattening of the fenestrindan skeleton caused by bridgehead substitution (cf. ref. [24 b])
    • b) According to our experience, MM calculations systematically underestimate the flattening of the fenestrindan skeleton caused by bridgehead substitution (cf. ref. [24 b]).
  • 70
  • 71
    • 0002852113 scopus 로고
    • (Eds.: R. B. King, D. H. Rouvray), Elsevier, Amsterdam
    • b) J. Simon in Graph Theory and Topology in Chemistry (Eds.: R. B. King, D. H. Rouvray), Elsevier, Amsterdam, 1987, pp. 43-75;
    • (1987) Graph Theory and Topology in Chemistry , pp. 43-75
    • Simon, J.1
  • 73
    • 0002430968 scopus 로고
    • For recent reviews on fenestrane chemistry, see: (Eds.: S. Patai, Z. Rappoport), Wiley, New York
    • For recent reviews on fenestrane chemistry, see: a) W. C. Agosta in The Chemistry of Alkanes and Cycloalkanes (Eds.: S. Patai, Z. Rappoport), Wiley, New York, 1992, pp. 927-962;
    • (1992) The Chemistry of Alkanes and Cycloalkanes , pp. 927-962
    • Agosta, W.C.1
  • 74
    • 0002384721 scopus 로고
    • (Eds.: J. Mulzer, H.-J. Altenbach, M. Braun, K. Krohn, H.-U. Reissig), VCH, Weinheim
    • b) K. Krohn in Organic Synthesis Highlights (Eds.: J. Mulzer, H.-J. Altenbach, M. Braun, K. Krohn, H.-U. Reissig), VCH, Weinheim, 1991, pp. 371-377;
    • (1991) Organic Synthesis Highlights , pp. 371-377
    • Krohn, K.1
  • 76
    • 84891458901 scopus 로고    scopus 로고
    • see also ref. [25 c]
    • d) see also ref. [25 c].
  • 77
    • 84891462486 scopus 로고    scopus 로고
    • note
    • Further details of the crystal structure investigation may be obtained from the Fachinformationszentrum Karlsruhe, D-76344 Eggenstein-Leopoldshafen (Germany), on quoting the depository number CSD 401770.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.