メタクロロ過安息香酸による2-メトキシー4<i>H</i>-1, 3, 2-ベンゾジオキサホスホリン2-スルフィド (サリチオン) のベンゾキサチオホスホリンへの異性化

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  • 呉 少勇
    Department of Agricultural Chemistry, Kyushu University
  • 江藤 守総
    Department of Agricultural Chemistry, Kyushu University

書誌事項

タイトル別名
  • Isomerization of 2-Methoxy-4<i>H</i>-1, 3, 2-benzodioxaphosphorin 2-Sulfide (Salithion) into Benzoxathiophosphorin by <i>m</i>-Chloroperbenzoic Acid
  • メタクロロ過安息香酸による2-メトキシー4H-1,3,2-ベンゾジオキサホスホリン2-スルフィド(サリチオン)のベンゾキサチオホスホリンへの異性化〔英文〕
  • メタクロ ロカ アンソクコウサン ニ ヨル 2 メトキシ 4H 1 3 2 ベ

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説明

The oxidative desulfurization of 2-methoxy-4H-1, 3, 2-benzodioxaphosphorin 2-sulfide (salithion) by m-chloroperbenzoic acid (MCPBA) produced an isomerized product 2-methoxy-4H-1, 3, 2-benzoxathiophosphorin 2-oxide (S-benzyl salithion) as well as the expected 2-methoxy-4H-1, 3, 2-benzodioxaphosphorin 2-oxide (salioxon). The isomerization was affected by reaction solvents; it proceeded easily in chloroform but was restrained by benzene and ether. Two derivatives of salithion, 6-chloro-2-methoxy-4-methyl-1, 3, 2-benzodioxaphosphorin 2-sulfide (CMMBS) and 2-ethoxy homolog (CEMBS), were also transformed into the respective S-benzyl isomers in different degrees by MCPBA. This type of isomerization was supposed to occur through a phosphorus oxythionate intermediate generally proposed for the MCPBA oxidation of P=S compounds. When incubated with a rat liver microsomal preparation, however, salithion did not yield any S-benzyl isomer.

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