| Project/Area Number |
10650834
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
有機工業化学
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| Research Institution | OKAYAMA UNIVERSITY |
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Principal Investigator |
TSUBOI Sadao Okayama University, Faculty of Environmental Science and Technology, Professor, 環境理工学部, 教授 (00032954)
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| Co-Investigator(Kenkyū-buntansha) |
HAYASHI Nobuyuki Okayama University, Faculty of Environmental Science and Technology, Assistant Professor, 環境理工学部, 助手 (40294441)
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| Project Period (FY) |
1998 – 1999
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| Project Status |
Completed (Fiscal Year 1999)
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| Budget Amount *help |
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 1999: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 1998: ¥2,500,000 (Direct Cost: ¥2,500,000)
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| Keywords | trichlorofluoromethane / abandoned chlorofluorocarbon / medicine / reagent for fluorination / biologically active compound / fluoromethyl phenyl sulfone / diphenyl disulfide / chlorofluoromethyl phenyl sulfone / フェニルジスルフィド / クロロフルオロメチルフェニルスホン / フロン11 / トリブチルホスフィン / フルオロエチレン / プロパルギルアルコール誘導体 / フルオロビニルケトン / フルオロアセトフェノン |
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| Research Abstract |
The aim of the present research is the utilization of chlorofluorocarbons (CFCs), especially CFC-11 for the synthesis of organointermediates, functional materials and biologically active compounds without decomposition.
In 1998, we succeeded in the synthesis of propargyl alcohols via basic treatment of fluoroethylenes, which were obtained from the reaction of CFC-11 with tributylphosphine.
In 1999, dichlorofluoromethyl phenyl sulfid (1) was prepared in a good yield by the reaction of CFC-11 with diphenyl disulfide. Oxidation of 1 with 30% hydrogen peroxide gave the corresponding sulfone 2 in 79% yield. Reduction of 2 with zinc afforded fluoromethyl phenyl sulfone (3) , which is an important organointermediate for the synthesis of fluorine-containing medicines such as antivirus agents and antibiotics.
These compounds were prepared by experimentally simple and economical methods. The application of its patent is under preparation. Reduction of 2 with an equivalent of zinc gave chlorofluoromethyl phenyl sulfone in 80% yield, which reacted with various carbonyl compounds, giving interesting rearrangement and addition products.
These results were reported to all of Japan in Yomiuri Shimbun (October 18 and 19, 1999) and also in Sanyo Shimbun (October 20, 1999). We also reported the above results in Asian Chemical Congress (Taipei, November 1999).
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