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Volumn 75, Issue 14, 2010, Pages 4748-4760

Probing the arenium-ion (ProtonTransfer) versus the cation-radical (Electron Transfer) mechanism of scholl reaction using DDQ as oxidant

Author keywords

[No Author keywords available]

Indexed keywords

C-C BOND FORMATION; CATION-RADICALS; ELECTRON DONORS; ELECTRON TRANSFER; EXPERIMENTAL EVIDENCE; FERRIC CHLORIDE; OXIDATION POTENTIALS;

EID: 77954557779     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100611k     Document Type: Article
Times cited : (199)

References (111)
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    • The calculated structures (DFT at B3LYP/6-31G* level) of various polyaromatic intermediates and their energies during the transformation of a representative hexaarylbenzene to the corresponding HBC clearly show that introduction of and increasing number of C-C bonds in a hexaarylbenzene leads to planarized polycyclic aromatic hydrocarbons with increasing aromaticity and thus decreased redox potentials and in turn leads to their increased reactivity towards the Scholl reaction.
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    • have ample literature precedent in the syntheses of a variety of biaryls, see: Hammerich, O.; Parker, V. D. in ref 11
    • Bauld, N. L.; Gao, D. J. Chem. Soc., Perkin 2 2000, 931) have ample literature precedent in the syntheses of a variety of biaryls, see: Hammerich, O.; Parker, V. D. in ref 11.
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    • 3-catalyzed tert -butylation of hexaphenylbenzene. (49)
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    • We also thank one of the reviewer for the suggestion to utilize magic blue as an oxidant to provide additional credence for the cation-radical mechanism for Scholl reaction
    • We also thank one of the reviewer for the suggestion to utilize magic blue as an oxidant to provide additional credence for the cation-radical mechanism for Scholl reaction.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.