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Volumn 13, Issue 7, 2011, Pages 1634-1637

Sequential oxidative transformation of tetraarylethylenes to 9,10-diarylphenanthrenes and dibenzo[g, p]chrysenes using DDQ as an oxidant

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EID: 79953209021     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200069c     Document Type: Article
Times cited : (108)

References (25)
  • 1
    • 67650992049 scopus 로고    scopus 로고
    • references cited therein
    • Heath, J. R. Annu. Rev. Mater. Res. 2009, 39, 1-23 and references cited therein
    • (2009) Annu. Rev. Mater. Res. , vol.39 , pp. 1-23
    • Heath, J.R.1
  • 16
    • 79953221386 scopus 로고    scopus 로고
    • An NMR analysis of the crude reaction mixture suggested that it contained traces of parent dibenzochrysene 1d and 9,10-diphenylphenathrene (1b) together with a multitude of products arising from the electrophilic aromatic chlorination of 1a, 1b, and 1d.
    • An NMR analysis of the crude reaction mixture suggested that it contained traces of parent dibenzochrysene 1d and 9,10-diphenylphenathrene (1b) together with a multitude of products arising from the electrophilic aromatic chlorination of 1a, 1b, and 1d.
  • 19
    • 79953165625 scopus 로고    scopus 로고
    • +2
    • +2.
  • 22
    • 0028063812 scopus 로고
    • Oxidative cyclizations of symmetrical TAEs to corresponding diarylphenanthrenes and diarylmethylidenefluorene have been previously observed; see
    • Oxidative cyclizations of symmetrical TAEs to corresponding diarylphenanthrenes and diarylmethylidenefluorene have been previously observed; see: Ciminale, F.; Lopez, L.; Mele, G. Tetrahedron 1994, 50, 12685
    • (1994) Tetrahedron , vol.50 , pp. 12685
    • Ciminale, F.1    Lopez, L.2    Mele, G.3
  • 23
    • 79953195064 scopus 로고    scopus 로고
    • It is well known that the cation radicals and dications of of TAEs are twisted around the ethylenic C=C bond by ∼30°-60° and undergo ready isomerization under oxidative conditions; see ref 11.
    • It is well known that the cation radicals and dications of of TAEs are twisted around the ethylenic C=C bond by ∼30°-60° and undergo ready isomerization under oxidative conditions; see ref 11.
  • 24
    • 0001758806 scopus 로고    scopus 로고
    • red = +0.60 V vs SCE), in the presence of an acid, oxidizes a variety of aromatic donors with oxidation potentials as high as ∼1.6 V vs SCE to the corresponding cation radicals; however, the rate of formation of these cation radicals decreases with the increasing oxidation potential of donors; see:;, and references cited therein
    • red = +0.60 V vs SCE), in the presence of an acid, oxidizes a variety of aromatic donors with oxidation potentials as high as ∼1.6 V vs SCE to the corresponding cation radicals; however, the rate of formation of these cation radicals decreases with the increasing oxidation potential of donors; see: Rathore, R.; Kochi, J. K. Acta Chem. Scand. 1998, 52, 114 and references cited therein
    • (1998) Acta Chem. Scand. , vol.52 , pp. 114
    • Rathore, R.1    Kochi, J.K.2
  • 25
    • 79953178512 scopus 로고
    • The bifluorenylidene formed from 2a, after oxidative C-C bond formation, can easily be isomerized to DBC 2d by an acid or electron-transfer catalysis; see:;, and references cited therein
    • The bifluorenylidene formed from 2a, after oxidative C-C bond formation, can easily be isomerized to DBC 2d by an acid or electron-transfer catalysis; see: Suzuki, K.; Yamaguchi, U. Bull. Chem. Soc. Jpn. 1962, 35, 735 and references cited therein
    • (1962) Bull. Chem. Soc. Jpn. , vol.35 , pp. 735
    • Suzuki, K.1    Yamaguchi, U.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.