Reduction of acetophenone using supercritical 2-propanol: the substituent effect and the deuterium kinetic isotope effect |
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Authors: | Takashi KamitanakaTomoko Matsuda Tadao Harada |
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Institution: | Department of Materials Chemistry, Faculty of Science and Technology, Ryukoku University, Otsu, Shiga 520-2194, Japan |
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Abstract: | The reductions of several substituted acetophenones using supercritical 2-propanol were carried out to estimate the Hammett's reaction constant (ρ=0.33). Also, the reduction of acetophenone using supercritical deuteriated 2-propanol was carried out to determine the rate-determining step. The kinetic isotope effects were observed in the reduction using 2-deuterio-2-propanol (kH/kD=1.6) and O-deuterio-2-propanol (kH/kD=2.0). These findings suggest that the reaction proceeds via a cyclic transition state between acetophenone and 2-propanol similar to that of the Meerwein-Ponndorf-Verley reduction. |
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Keywords: | supercritical 2-propanol reduction Meerwein-Ponndorf-Verley reduction Hammett equation kinetic isotope effect acetophenone |
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