1995 Fiscal Year Final Research Report Summary
Synthesis of Deuterium Labelling Organic Compounds
| Project/Area Number |
06650993
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
有機工業化学
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| Research Institution | Ube National College of Technology, Department of Chemical and biological Engineering |
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Principal Investigator |
KAKINAMI Takaaki Ube National College of Technology, Department of Chemical and Biological Engineering, Assistant Professor, 物質工学科, 助教授 (30224348)
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| Co-Investigator(Kenkyū-buntansha) |
TASHIRO Masashi Kyushu University, Professor, 機能物質科学研究所, 教授 (40038576)
MATAKA Shuntaro Kyusyu University, Assistant Professor (10038599)
TSUKINOKI Takehito Tohwa University, Lecturer
TSUZUKI Hirohisa Kyushu University, Central Analytical Center
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| Project Period (FY) |
1994 – 1995
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| Keywords | Deuterium Labelling / Synthesis / Raney-Alloy / BaO-D_2O / Na_2CO_3-D_2O / d_<11>-シクロヘキサノール / ベンジルアルコール / 2-フェニルエタノール |
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| Research Abstract |
The authors develop composition method of deutriated organic compounds triggering various kinds of raney-alloys during sodium deutroxide (NaOD) as an method to introduced deuterium into and organic compounds. However, NaOD is expensive, so cannot use in laboratory. Now, we found new deuteration methods for organic compounds use easily in laboratory. For example, the reductive debromination of bromophenol derivatives with Cu-Al alloy in a D_2O solution of sodium carbonate or barium oxide at 60ﾟC under a nitrogen atomsphere gives ring-deutriated phenol derivatives in good yields and in high isotopic purities. Futhermore, by use of raney Ni-Al alloy in a saturated Ba(OH)_2 solution, halophenols are easily hydrogenated at mild temperature and at atomspheric pressure, giving the corresponding cyclohexanols. Reduction of pentachlorophenol with raney Ni-Al alloy in saturated BaO-D_2O under sonication afforded D_<11-> cyclohexanol in 85% yieldwith a high D-content (99%). Various haloanilines and benzylnitriles were treated in a 1.25N Na_2CO_3 solution with raney Cu-Al or Ni-Al alloy. In the case of haloanilines, dehalogenated anilines were obtained in good yield. On the other hand, the reduction of benzylnitriles afforded the corresponding 2-arylethylamines. The reduction of aromatic nitrile compounds such as benzonitriles and benzylnitriles with raney-alloys in a surfuryl chloride solution under acidic conditions gives benzylalcohols and phenylethylalcohols in fairly good yield, respectively.
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