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Volumn 8, Issue 6, 2006, Pages 1197-1200

Novel synthesis of bridged phenylthienylethenes and dithienylethenes via Pd-catalyzed double-cyclization reactions of diarylhexadienynes

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EID: 33646463437     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0600281     Document Type: Article
Times cited : (39)

References (33)
  • 9
    • 0348080703 scopus 로고    scopus 로고
    • Special issue on photochromism: Irie, M. Chem. Rev. 2000, 100, 1685.
    • (2000) Chem. Rev. , vol.100 , pp. 1685
    • Irie, M.1
  • 11
  • 15
    • 0037158198 scopus 로고    scopus 로고
    • We also reported 6-endo tandem cyclization of diaryldienynes by flash vacuum pyrolysis (FVP): (b) Sonoda, M.; Itahashi, K.; Tobe, Y. Tetrahedron Lett. 2002, 43, 5269.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 5269
    • Sonoda, M.1    Itahashi, K.2    Tobe, Y.3
  • 16
  • 19
    • 33646462923 scopus 로고    scopus 로고
    • note
    • (Z)-Biindenylidenes should be deformed to a nonplanar conformation because of the steric hindrance between the two inner peri hydrogen atoms. According to the calculations by the DFT method at the B3LYP/6-31G** level, twist angles of the central double bond of (E)- and (Z)-biindenylidenes were estimated to be 0° and 14.9°, respectively.
  • 20
    • 33646454758 scopus 로고    scopus 로고
    • note
    • The DFT calculations at the B3LYP/6-31G** level predict that the twist angles of the central double bond of (Z)-isomers of 9a, 9b, and 9c are 11.4°, 6.1°, and 8.4°, respectively, whereas those of both 9d and 9e are 0°. The corresponding angles of the (E)-isomers, (E)-9a-e, are essentially 0°.
  • 24
    • 33646449838 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra, which showed sets of vinyl proton signals with J ∼ 16 Hz (δ 7.45 and 6.43 ppm for (E,Z)-2a and δ 7.36 and 6.38 ppm for (E,Z)-2b) and those with J ∼ 12 Hz (δ 6.96 and 5.73 ppm for (E,Z)-2a and δ 6.73 and 5.78 ppm for (E,Z)-2b).
  • 25
    • 33646448928 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum of the residual fractions after isolation of pure (Z,Z)-isomer using preparative GPC. Thus, two doublet of doublet signals, due to the vinyl protons adjacent to the acetylenic carbons, with J ∼ 12 Hz (δ 5.84 and 5.71 ppm) and four doublet of doublet signals with J ∼ 16 Hz (δ 6.32, 6.25, 6.19, and 6.14 ppm) were assigned to the two (E,Z)- and (E,E)-isomers. The vinyl proton signals adjacent to aromatic rings, which appeared at lower field, were concealed by the aromatic proton signals. Simiarly, a doublet of doublet signal with J ∼ 16 Hz at δ 6.27 ppm and that with J ∼ 12 Hz at δ 5.85 ppm in the spectrum of 2d were ascribed to (E,Z)-2d.
  • 28
    • 33646462489 scopus 로고    scopus 로고
    • note
    • 3). It was not possible, therefore, to measure the absorption spectrum of (Z)-9a accurately.
  • 29
    • 33646440194 scopus 로고    scopus 로고
    • note
    • The low yields of 9c and 9d were partly ascribed to the decomposition of the products under the reaction conditions.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.