Synthesis of New Synthons for Organofluorine Compounds from Halothane Containing Sulfur Functional Groups
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概要
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To develop new synthons for the syntheses of organofluorine compounds, the treatment of Halothane, 2-bromo-2-chloro-1,1,1-trifluoroethane, (1) with 4-methylbenzenethiol (2) in the presnce of sodium hydride gave 1-chloro-2,2,2-trifluoroethyl 4-methylphenyl sulfide (3), which was oxidized with m-chloroperbenzoic acid (m-CPBA) to the corresponding sulfoxide (4) and sulfone (5). Reaction of 3 and 5 with allyltributyltin in the presence of 2,2'-azobis(isobutyronitrile) (AIBN) gave 1-(trifluoromethyl)-3-butenyl compounds (9,11). Sulfoxide 4 was decomposed in this condition. The treatment of 3 with allyltrimethylsilane in the presence of Lewis acids gave 1-(trifluoromethyl)-3-butenyl compounds (9) in good yield. This result suggests taht 4-methylphenylthio substituent stabilizes the α-carbocation effectively, though the trifluoromethyl group destabilizes it strongly. Aromatic compounds similarly reacted with 3 in the presence of titanium(IV) chloride to give 2-aryl-1,1,1-trifluoro-2-(4-methylphenylthio)ethanes. Thus, sulfur compounds derived from Halothane were found to be useful new synthons for organofluorine compounds.
- 公益社団法人日本薬学会の論文
- 2000-05-01
著者
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安藤 章
Faculty of Pharmaceutical Sciences, Setsunan University
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Ando A
Faculty Of Pharmaceutical Sciences Setsunan University
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加藤 昌子
Div. Of Chemistry Fac. And Graduate School Of Sci. Hokkaido Univ.
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Sato K
National Inst. Health Sci. Tokyo Jpn
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OMOTE Masaaki
Faculty of Pharmaceutical Sciences
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ANDO Akira
Faculty of Pharmaceutical Sciences
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KUMADAKI Itsumaro
Faculty of Pharmaceutical Sciences
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Maeda K
Faculty Of Pharmaceutical Sciences Setsunan University
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KATO Makoto
Faculty of Pharmaceutical Sciences, Setsunan University
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MAEDA Kensuke
Faculty of Pharmaceutical Sciences, Setsunan University
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SATO Kazuyuki
Faculty of Pharmaceutical Sciences, Setsunan University
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Omote M
Faculty Of Pharmaceutical Sciences Setsunan University
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Kato Makoto
Faculty Of Agriculture Tokyo University Of Agriculture And Technology
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Kumadaki I
Faculty Of Pharmaceutical Sciences Setsunan University
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