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Volumn 7, Issue 24, 2001, Pages 5382-5390

Synthesis, spectroscopic, and structural properties of spirocyclopropanated bicyclobutylidenes and their radical cations

Author keywords

Bicyclobutylidenes; Conjugation; Density functional calculations; Radical ions; Small ring systems

Indexed keywords

CHEMICAL BONDS; OXIDATION; POSITIVE IONS; SPECTROSCOPIC ANALYSIS; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

EID: 0035905366     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20011217)7:24<5382::AID-CHEM5382>3.0.CO;2-Y     Document Type: Article
Times cited : (12)

References (74)
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    • note
    • v) of 1,1-di-, cis-1,2-di-, trans-1,2-di-, and tricyclopropylethene (8.08, 7.70, 7.72, and 7.48 eV, respectively) were off scale from that more recently obtained by us for tetracyclopropylethene (1) (7.90 eV), they were redetermined and found to be 8.80, 8.50, 8.40, and 8.0 eV, respectively.
  • 26
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    • b) L. Fitjer, Chem. Ber. 1982, 115, 1047-1060;
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    • -3. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-163 390 (2a), CCDC-161 506 (5) and 161 507 (10). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+44) 1223-336-033; e-mail: deposit@ ccdc.cam.ac.uk).
    • (1994) Organic Crystal Chemistry , pp. 20-37
    • Boese, R.1    Nussbaumer, M.2
  • 45
    • 33845283526 scopus 로고
    • Theoretical calculations using different ab initio methods (STO-3G, 3-21G, 4-21G) underestimated the length of the central C=C bond in 2a, but semiempirical calculations by the MNDO method gave a surprisingly accurate prediction. See: M. Eckert-Maksic, Z. B. Maksic, A. Skancke, P. N. Skancke, J. Phys. Chem. 1987, 91, 2786-2790.
    • (1987) J. Phys. Chem. , vol.91 , pp. 2786-2790
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  • 46
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    • The normal reactivity of the parent bicyclobutylidene (2a) has been demonstrated by the addition of bromine, cheletropic cycloadditions of methylene, dibromocarbene, cyclopropylidene, cyclobutylidene, [2 + 2] cycloadditions of ketenes and even metathesis reactions: a) L. K. Bee, J. W. Everett, P. J. Garratt, Tetrahedron 1977, 33, 2143-2150;
    • (1977) Tetrahedron , vol.33 , pp. 2143-2150
    • Bee, L.K.1    Everett, J.W.2    Garratt, P.J.3
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    • Angew. Chem. Int. Ed. 2000, 39, 2495-2498;
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 2495-2498
  • 55
    • 84918386253 scopus 로고
    • Tetracyclopropylethene as well as tetraisopropylethene also did not add dichlorocarbene: E. V. Dehmlow, A. Eulenberder, Liebigs Ann. Chem. 1979, 1112-1115.
    • (1979) Liebigs Ann. Chem. , pp. 1112-1115
    • Dehmlow, E.V.1    Eulenberder, A.2
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    • note
    • 3-hybridized carbon atoms from a π center are denoted α, β, γ, δ, etc., respectively.
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    • A cylindrical cell with a helical gold anode and a platinum-wire cathode in the cell was used. See: H. Ohya-Nishiguchi, Bull. Chem. Soc. Jpn. 1979, 52, 2064-2068.
    • (1979) Bull. Chem. Soc. Jpn. , vol.52 , pp. 2064-2068
    • Ohya-Nishiguchi, H.1
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    • (Ed.: H. F. Schaefer, III), Plenum
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    • Pulay, P.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.