o-Quinodimethane generation from .ALPHA.,.ALPHA.'-dihalo-o-xylenes by use of sodium benzenetellurolate.
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概要
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Treatment of α,α′-dihalo-<I>o</I>-xylenes with sodium benzenetellurolate gave <I>o</I>-quinodimethane which readily reacted with dienophiles leading to Diels–Alder adducts. The best yields were obtained when the reaction was carried out in refluxing ethanol using two molar equivalents of the benzenetellurolate to α,α′-dihalo-<I>o</I>-xylenes. This reaction competes with substitution of the halogen atoms with the benzenetellurolate anion to afford α,α′-bis(phenyltelluro)-<I>o</I>-xylene, which did not give <I>o</I>-quinodimethane under identical conditions. It is likely that the reaction proceeds through nucleophilic attack of benzenetellurolate anion at the tellurium atom of α-halo-α′-phenyltelluro-<I>o</I>-xylene which is formed in situ by the substitution of one of the halogen atoms of the starting α,α′-dihalo-<I>o</I>-xylene with the benzenetellurolate anion. When sodium benzeneselenolate was employed, no evidence of <I>o</I>-quinodimethane formation was observed under similar conditions.
- 公益社団法人 日本化学会の論文
著者
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Kambe Nobuaki
Department Of Applied Chemistry And Center For Atomic And Molecular Technologies Graduate School Of
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Murai Shinji
Department af Chemical Technology Faculty of Engineering Osaka University
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Sonoda Noboru
Department af Chemical Technology Faculty of Engineering Osaka University
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Tsukamoto Takashi
Department of Applied Chemistry, Faculty of Engineering, Osaka University
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Miyoshi Noritaka
Department of Applied Chemistry, Faculty of Engineering, Osaka University
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