Ring-opening reaction of oxiranes, oxetanes, and tetrahydropyran by mercury(II) salts and alkyl halides.

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概要

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• The reaction of primary and secondary alkyl halides with mercury(II) acetate in oxiranes, oxetanes, and tetrahydropyran results in ring-opening to give the corresponding alkoxyalkyl acetates. Similar reactions with mercury(II) thiocyanate in oxetanes afford alkoxyalkyl isothiocyanate and thiocyanate, ROCH<SUB>2</SUB>C(R′)<SUB>2</SUB>CH<SUB>2</SUB>NCS and ROCH<SUB>2</SUB>C(R′)<SUB>2</SUB>CH<SUB>2</SUB>SCN, where the isomer ratios (N/S ratios) are 82–96/4–18. It is suggested that the reactions involve the initial formation of a three-, four-, or six-membered <I>O</I>-alkyloxonium ion intermediate and subsequent attack by XHgZ<SUB>2</SUB><SUP>−</SUP>.

• 公益社団法人 日本化学会の論文

著者

• Okano Masaya

  Institute for Chemical Research, Kyoto University

• Uemura Sakae

  Institute for Chemical Research, Kyoto University

• Watanabe Nanao

  Koei Chemical Co. Ltd.

• Watanabe Nanao

  Koei Chemical Co., Ltd.

関連論文

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• Oxidation of olefins with thallium(III) acetate in diols.

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