RESEARCH ON HIGH EFFICIENT PROCESS UTILIZING HYPERVALENT IODINE COMPOUNDS

高价碘化合物高效利用工艺研究

基本信息

  • 批准号:
    05640668
  • 负责人:
  • 金额:
    $ 1.34万
  • 依托单位:
  • 依托单位国家:
    日本
  • 项目类别:
    Grant-in-Aid for General Scientific Research (C)
  • 财政年份:
    1993
  • 资助国家:
    日本
  • 起止时间:
    1993 至 1994
  • 项目状态:
    已结题

项目摘要

The aim of this research was devoted to develop new high efficient process for synthesis of organic compounds by utilizing hypervalent iodine compounds, especially (p-phenylene) bisiodonium salts.1. Synthesis of (p-phenylene) bisiodonium saltsA new bisiodine (III) reagent was prepared from iodosylbenzene and trifluoromethanesulfonic acid and used to prepare the (p-phenylene) bisiodonium salts by reaction with aromatic substrates and acetylenic compounds.Furthermore, new types of hypervalent iodine reagents were obtained from iodobenzene diacetate and o-iodosylbenzoic acid.2. Reaction of (p-phenylene) bisiodonium salts with nucleophilesReaction of alkynyl (p-phenylene) bisiodonium salts with thiocyanate ion gave alkynylthiocyanates but the reaction with the enolate of phenylindanedione and phenoxide ion provided pentene and benzofuran derivatives, respectively. Although the (p-phenylene) bisiodonium salts showed a high reactivity to nucleophiles, the reaction proceeded via a Michael addition-rearrangement process. Reaction with alkynylcopper reagents gave diacetylene derivatives and was applied to synthesis of liquid-crystalline diacetylenes.Aryl (p-phenylene) bisiodonium salts reacted with pyridine, triphenylphosphine, and diphenyl sulfide. l-Arylbenzothiophenium salts were prepared in a similar manner.
这项研究的目的是开发利用高价碘化合物,特别是(对苯基)双碘盐合成有机化合物的新的高效工艺。以碘代苯和三氟甲磺酸为原料合成了一种新的二硅碘(III)试剂,并将其与芳香族底物和乙酰化合物反应制备了(对苯基)双碘盐,进而以二乙酸碘苯和邻碘苯甲酸为原料合成了新型的高价碘试剂。(对苯基)双碘盐与亲核剂的反应炔基(对苯基)双碘盐与硫氰酸根离子反应生成炔基硫氰酸酯,而与苯基吲哚二酮和苯氧根离子反应分别生成戊烯和苯并呋喃衍生物。尽管(对苯基)双碘盐对亲核试剂表现出很高的反应活性,但反应是通过Michael加成-重排过程进行的。芳基(对苯基)双碘盐与吡啶、三苯基膦、二苯硫醚反应生成二乙炔衍生物。用类似的方法制备了L-芳基苯并硫苯盐。

项目成果

期刊论文数量(34)
专著数量(0)
科研奖励数量(0)
会议论文数量(0)
专利数量(0)
北村二雄: "1-[(Hydroxy)(trifyloxy)iodo]-4-[(phenyl)(trifyloxy)iodo]benzene as a Reactive Organoiodine(III)Reagent:Isolation and Characterization" Synlett. 193-194 (1993)
Futoshio Kitamura:“1-[(羟基)(三甲氧基)碘]-4-[(苯基)(三甲氧基)碘]苯作为反应性有机碘(III)试剂:分离和表征”Synlett 193-194(1993)。
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Tsugio, Kitamura, Chi Han Lee, Hiroshi, Taniguchi, Masaru, Matsumoto, and Sano, Youich: "Preparation and Coupling Reactions of Alkynyl (phenyl) iodonium Salts Bearing Long Alkoxy Chains.Formation of Liquid-Crystalline Diacetylenes" Journal of Organic Chem
Tsugio、Kitamura、Chi Han Lee、Hiroshi、Taniguchi、Masaru、Matsumoto 和 Sano, Youich:“带有长烷氧基链的炔基(苯基)碘盐的制备和偶联反应。液晶二乙炔的形成”有机化学杂志
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北村二雄・谷口宏他3名: "Preparation and Crystal Structure of a Parent l-Arylbenzo[b]thiophennium Triflate and Its Derivatives" Chemistry Letters. 1703-1706 (1993)
Futoshi Kitamura、Hiroshi Taniguchi 等 3 人:“母体 L-芳基苯并[b]噻吩鎓三氟甲磺酸酯及其衍生物的制备和晶体结构”化学快报 1703-1706 (1993)。
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北村二雄: "Preparation and Crystal Structure of a Parent 1-Arylbenzo[b]thiophenium Triflate and Its Derivaties" Chemistry Letters. 1703-1706 (1993)
Futoshi Kitamura:“母体 1-芳基苯并[b]噻吩鎓三氟甲磺酸盐及其衍生物的制备和晶体结构”化学快报 1703-1706 (1993)。
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北村二雄: "Novel Cyclization to Benzofurans in the Reaction of Alkynyl(p-phenylene)bisiodonium Ditriflates with Phenoxide Anion" Tetrahedron Letters. 34. 4055-4058 (1993)
Futoshi Kitamura:“炔基(对亚苯基)二碘鎓二三氟甲磺酸盐与酚盐阴离子反应中新型苯并呋喃环化”四面体快报 34. 4055-4058 (1993)
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KITAMURA Tsugio其他文献

KITAMURA Tsugio的其他文献

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{{ truncateString('KITAMURA Tsugio', 18)}}的其他基金

Development of New Fluorination Reactions Aiming for Conversion of Raw Materials in Fluorination
旨在实现氟化原料转化的新型氟化反应的开发
  • 批准号:
    16K05703
  • 财政年份:
    2016
  • 资助金额:
    $ 1.34万
  • 项目类别:
    Grant-in-Aid for Scientific Research (C)
Development of Hypervalent Iodine Compounds for New Medicines and Agricultural Chemicals
新药及农用化学品用高价碘化合物的开发
  • 批准号:
    12555257
  • 财政年份:
    2000
  • 资助金额:
    $ 1.34万
  • 项目类别:
    Grant-in-Aid for Scientific Research (B)
Selective Synthesis and Application of Novel Liquid-Crystalline Diaryldiacetylenes
新型液晶二芳基二乙炔的选择性合成及应用
  • 批准号:
    09450334
  • 财政年份:
    1997
  • 资助金额:
    $ 1.34万
  • 项目类别:
    Grant-in-Aid for Scientific Research (B).
DEVELOPMENT OF HIGHLY EFFICIENT BENZYNE TRANSFORMATION PROCESS USING HYPERVALENT IODINE COMPOUNDS
利用高价碘化合物开发高效苯转化工艺
  • 批准号:
    07804046
  • 财政年份:
    1995
  • 资助金额:
    $ 1.34万
  • 项目类别:
    Grant-in-Aid for Scientific Research (C)
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