Selenium Dioxide Oxidation of lsoprene

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  • TANAKA Juntaro
    Department of Synthetic Chemistry, Faculty o Engineering, Shizuoka University
  • SUZUKI Toshihiro
    Department of Synthetic Chemistry, Faculty o Engineering, Shizuoka University
  • TAKABE Kunihiko
    Department of Synthetic Chemistry, Faculty o Engineering, Shizuoka University
  • KATAGIRI Takao
    Department of Synthetic Chemistry, Faculty o Engineering, Shizuoka University

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Other Title
  • 二酸化セレンによるイソプレンの酸化

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Description

Selenium dioxide oxidation of isoprene was investigated. The oxidation products identified were 2-hydroxymethyl-1, 3-butadiene(1), 2-acetoxymethyl-1, 3-butadiene(2), 3-acetoxymethylfuran(3), 1-formyl-3 or 4-methyl-1-vinylcyclohex-3-ene(4), 2-methyl-1, 4-diacetoxy-2-butene (5), 2-formyl-4-acetoxy-2-butene(6), 3-hydroxy-4-methylenetetrahydroselenophene(7), 3-acetoxy-4-methylenetetrahydroselenophene(8), 4-acetoxy--3-hydroxy-3-methyltetrahydroselenophene(9) and 3, 4-djacetoxy-3-methyltetrahydroselenophene.(10)<BR>The composition of these products was dependent on the molar ratio of iseprene to selenium dioxide and the solvents when the ratio was (10), the main product was (1) and when it was 2, (8) and (9) were mainly obtained in acetic acid at 100-105c for 1hr. In the case of acetic anhydride, (6) was obtained as the main product.<BR>The selenium dioxide oxidations of (1) and (5) were also studied.<BR>From these results, the reaction scheme was discussed.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1973 (2), 292-295, 1973-02-10

    The Chemical Society of Japan

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