Reduction of Naphthalene in Hexamethylphosphoric triamide-Alkali metal-Proton donor Systems

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  • ヘキサメチルリン酸トリアミド-アルカリ金属-プロトンドナー系におけるナフタレンの還元反応

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The reduction of naphthaIene in hexamethylphosphoric triamide(HMPA)-alka1i meta1-p on donor systems was examined.<BR>The order of reagent addition did not affect the conversion of naphthalene and the selectivityof reaction.<BR>The kind of alkali metals affected the conversion, the selectivity(Table 3), and the effectiveness of alkali metals (Table 4). Therefore, the active species are supposed to be the solvated electrons formed in the HMPA solution of alkali metals, and the complexes of alkali metal iens and solvated electrons.<BR>There is no close correlation between the acidity of proton denors and the degree of reduction, the conversion (Table 1), and the effectiveness (Table 2). Thus, the direct reaction of alkali metal with the proton donor must be considered asst a side reaction when a strongly acidic proton donor was used (Equation(1'))<BR>1, 2-Dihydronaphthalene was obtained selectively when cyclohexylamine was used as a hydrogen source (Table 7). The reaction would proeeed in two succesive steps (Fig. 2).<BR>The selectivity of reduction varied with the change of the molar ratio ef alkali metal to the proton donor in the reaction system (Tables 5 and 7). However, the result did not agree with that of the reduction of benzene in liq. NH3-Na-H2O systems.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1973 (2), 308-313, 1973-02-10

    The Chemical Society of Japan

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