Reduction of acetophenone using supercritical 2-propanol: the substituent effect and the deuterium kinetic isotope effect

✍ Scribed by Takashi Kamitanaka; Tomoko Matsuda; Tadao Harada

• Book ID: 104253690
• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 105 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(03)00975-4

✦ Synopsis

The reductions of several substituted acetophenones using supercritical 2-propanol were carried out to estimate the Hammett's reaction constant (z=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-2propanol (k H /k D =1.6) and O-deuterio-2-propanol (k H /k D =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.