Nucleophilic substitution inO-phenyldibenzofuranium and 10-phenylxanthonium cations |
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| Authors: | T P Tolstaya M S Bobyleva A N Vanchikov G V Kovalysheva N S Kulikov D A Tsariev |
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| Institution: | 1. Department of Chemistry, M. V. Lomonosov Moscow State University, Vorob’evy Gory, 119899, Moscow, Russian Federation
2. K. A. Timiryazev Moscow Agricultural Academy, 49 ul. Timiryazevskaya, 127550, Moscow, Russian Federation
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| Abstract: | Reactions ofO-phenyldibenzofuranium tetrafluoroborate with nucleophiles (OH?, NO2 ?, AcO?) in aqueous media follow the SNAr-mechanism and involve dehydroarenes. In DMSO, this salt smoothly reacts with NO2 ? and I? with predominant opening of the furan ring. 10-Phenylxanthonium tetrafluoroborate readily arylates the NO2 ? ion in water (at the N and O atoms), mainly with predominant opening of the central ring, and is completely decomposed even with weak bases (NH2OH, 2,4-dinitrophenylhydrazine). The Bayer—Villiger oxidation of this salt affords xanthone and 2-phenoxybenzoic acid. |
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