Epoxide Rearrangement II. Isomerization of 1-Methylcyclohexene Oxide over Solid Acids and Bases

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概要

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• The reaction of 1-methylcyclohexene oxide over solid acids and bases at 108 °C was found to give five main products, 2-methylcyclohexanone (III), 1-methylcyclohexanol (IV), 2-methyl-2-cyclohexene-1-one (V), 2-methyl-enecyclohexanol (VIa), and 2-methyl-2-cyclohexene-1-ol (VIb), with a small amount of 1-methylcyclohexene (I) and unidentified compound (II). The ketone (III) was formed predominantly over zeolite, SiO<SUB>2</SUB>–Al<SUB>2</SUB>O<SUB>3</SUB>, H<SUB>2</SUB>SO<SUB>4</SUB>/SiO<SUB>2</SUB>, AlCl<SUB>3</SUB>, and BBr<SUB>3</SUB>, while the allyl alcohol (VI) was given by Al<SUB>2</SUB>O<SUB>3</SUB> and TiO<SUB>2</SUB>. HCl/SiO<SUB>2</SUB> and solid H<SUB>3</SUB>PO<SUB>4</SUB> calcined at 400–900°C gave both products, III and VI, in the same amounts, though the latter calcined at 200–300°C formed almost 100% ketone. Solid lithium perchlorate was surprisingly active for the formation of ketone, but other metal per chlorates and lithium salts were quite inactive. Alkaline earth metal oxides and NaOH/SiO<SUB>2</SUB> were almost inactive. The catalytic activity and selectivity as well as the reaction path and mechanism are briefly discussed mainly in connection with acid-base property of solid catalysts.

• 公益社団法人 日本化学会の論文

著者

• Tanabe Kozo

  Department of Chemistry, Faculty of Science, Hokkaido University

• Arata Kazushi

  Department of Chemistry, Hokkaido University of Education

• Akutagawa Susumu

  Central Research Laboratory, Takasago Perfumery Co.

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