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Chinese Journal of chemistry 1991年第4期9卷 351-359页

作者： huang,wei-yuan XIE,yuan shanghai institute of organic chemistry,academia sinica,shanghai 200032

The reaction of perfluoroalkyl iodide or perfluoroalkyl bromide with sulfite radical anion (SO_3^-)generated from sodium bisulfite/potassium ferricyanide in water/DMF at 70—75°C gave the corresponding perfluoroalkanesulfinate ia good ***,it was shown that the reagent system can also initiate the addition of perfluoroalkyl iodide to olefins or alkynes at 50—65℃.

关键词： Synthesis of 2-perfluoroalkyl-2-deoxy-D-glucose,mono and poly-O-polyfluoroalkylated-D-glucoses Studies on sulfinatodehalogenation

The nucleophilic reaction of polyfluoroaromatic compounds——II. The nucleophilic cyclization of chloropentafluorobenzene

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Chinese Journal of chemistry 1988年第3期6卷 238-243页

作者： GE Wen-Zheng HU Li-Qing huang wei-yuan**, shanghai institute of organic chemistry academia sinica, shanghai shanghai institute of organic chemistry academia sinica Shanghai

The results of cyclization reaction between chloropentafluorobenzene and bifunctionalnucleophiles such as XCH2CH2OH（X =OH, NHMe, NHEt） and HN （CH2CH2OH）2, NH2CH2CH2NH2were reported. It was found that the NaH/DMF system was a better reagent for the preparation ofsodium alcoholates and the yields of cyclic products ranged from 50-80% which were muchhigher than that reported by previous workers.3

关键词： The nucleophilic cyclization of chloropentafluorobenzene The nucleophilic reaction of polyfluoroaromatic compounds II

Studies on the reaction of cupric(Ⅱ)perfluoroalkanesulfinate

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Chinese Journal of chemistry 1990年第3期8卷 259-264页

作者： huang,wei-yuan XIE,yuan shanghai institute of organic chemistry,academia sinica,shanghai 200032

Reaction of aqueous solution of sodium perfluoroalkanesulfinate with cupric sulphate gave a high yield of cupric perfluoroalkanesulfinate,which decomposed slowly in the air on exposure to light to give perfluorocarboxylic *** reaction between cupric perfluoroalkanesulfinate and olefins in the presence of potassium iodide and excess CuSO_4 in ether at low temperature(-30 to-20℃)for- med two kinds of adducts,namely the normal adducts,R_fSO_2CH_2CHIR(2)and the adducts resulting from the loss of SO_2 moiety,R_f CH_2CHIR(3)in yields ranging from morderate to *** results were identical with that of the addition of perfluoroalkanesulfonyl iodide to olefins.A radical reac- tion mechanism is proposed.

关键词： CI Studies on the reaction of cupric perfluoroalkanesulfinate

Nucleophilic substitution reaction in polyfluoroaromaticsⅠ.Reactions with secondary amine nucleophiles

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Chinese Journal of chemistry 1985年第4期 349-355页

作者： GE Wen-Zheng WU Bao-Ming huang wei-yuan* shanghai institute of organic chemistry,academia sinica,shanghai

Perfluorobenzene,chloropentafluorobenzene and dichlorotetrafluorobenzene werereacted with pyrrolidine,piperidine,morpholine,diethylamine and dipropylamine in aprotic polarsolvents such as DMF and *** perfluorobenzene monosubstituted products were *** reaction time or raising the reaction temperature caused the formation of the para disub-stituted products in *** chloropentafluorobenzene,only the para substituted products wereobtained in *** was available as an isomeric mixtures of m:o:p=73:18:*** pyrrolidine,only the m-and o-dichlorotetrafluorobenzene reacted with the secondary amines toform the expected *** is because of the fact that reaction in polar solvents favors theformation of the products with substituent para to chlorine,but the p-dichlorotetrafluorobenzenehas no para fluorine to be *** the most active pyrrolidine however,attack at the positionortho to chlorine *** activity sequence of these secondary amine nucleophiles are attributed to both steric andpolar ***>piperidine>morpholine>diethylamine>dipropylamine>diisopropylamineAll of the products were identified by NMR,IR,GLC and elemental analyses and isomeric ratioswere calculated from quantitative NMR measurements.

关键词： NC Nucleophilic substitution reaction in polyfluoroaromatics Reactions with secondary amine nucleophiles

Studies on sulfinatodehalogenation——Ⅳ. The sulfinatodebromination of primary perfluoroalkyl bromides and perfluoroalkylene α, ω-dibromides

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Chinese Journal of chemistry 1986年第1期 68-72页

作者： huang Bing-Nan WANG Bing-huang WANG wei huang wei-yuan* shanghai institute of organic chemistry, academia sinica, shanghai

Using PTC or cosolvent, both perfluoroalkyl bromides such as Br （CF2）2O（CF2）2SO2Na （1）,Br（CF2）2OCF2CO2H （2）, Cl（CF2）4Br （3）, Cl（CF2）6Br （4）, n-C6F13Br （5）, n-C8F17Br （6）, H（CF2）8Br（7）, α, ω-dibromides O（CF2CF2Br）2（8）, Br（CF2）6Br （9） and Br（CF2）8Br （10） reacted readily withNa2S2O4in the presence of NaHCO3in aqueous solution to form the corresponding perfluoroalkanesulfinates NaO2S （CF2）2O（CF2）2SO2Na （11）, NaO2S（CF2）2OCF2CO2Na （12）, Cl （CF2）4SO2Na（13）, Cl（CF2）6SO2Na （14）, n-C6F13SO2Na （15）, n-C8F17SO2Na （16）, H（CF2）8SO2Na （17）, α, ω-disulfinates O（CF2CF2SO2Na）2（18）, NaO2S（CF2）6SO2Na （19） and NaO2S（CF2）8SO2Na （20） in66-97% yields. To this new and general reaction of perfluoroalkyl bromides, the namesulfinatodebromination is proposed.

关键词： The sulfinatodebromination of primary perfluoroalkyl bromides and perfluoroalkylene Studies on sulfinatodehalogenation

多氟芳烃的亲核反应 Ⅱ.一氯五氟苯的亲核环化

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化学学报 1988年第11期46卷 1109-1112页

作者：葛文正胡里清黄维垣中国科学院上海有机化学研究所上海

本文报道一氯五氟苯与双官能团亲核试剂反应制备环化产物的研究结果,发现应用NaH-DMF体系制备醇钠,有利于亲核反应的顺利进行,环化产物产率有较大幅度提高.

关键词：邻位双官能团环化产物亲核试剂类阴离子试剂产率 DMF 甲酰胺亲核反应 ppm 芳烃

多氟芳烃的亲核反应——Ⅰ.仲胺作为亲核试剂

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化学学报 1985年第9期43卷 859-864页

作者：葛文正吴宝明黄维垣中国科学院上海有机化学研究所中国科学院上海有机化学研究所上海上海

本文报道全氟苯、一氯五氟苯和二氯四氟苯与仲胺在DMF或HMPA中的亲核反应结果。C6F5Cl与仲胺反应生成对位产物。C6F4Cl2（m:o:p=73:18:9）与仲胺的反应,只有m-和o-异构体能生成预期产物,而p-C6F4Cl2只与活性高的四氢吡咯反应。延长反应... 详细信息

本文报道全氟苯、一氯五氟苯和二氯四氟苯与仲胺在DMF或HMPA中的亲核反应结果。C6F5Cl与仲胺反应生成对位产物。C6F4Cl2（m:o:p=73:18:9）与仲胺的反应,只有m-和o-异构体能生成预期产物,而p-C6F4Cl2只与活性高的四氢吡咯反应。延长反应时间和提高反应温度,C6F6可给出对位双取代产物。六个仲胺的反应活性顺序是:四氢吡咯>哌啶>吗啡啉>二乙胺>二正丙胺>二异丙胺。

关键词：亲核反应仲胺亲核试剂二正丙胺吗啡啉五氟苯二异丙胺加成物二乙胺反应结果

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丁基苯的三氟化钴气相氟化

化学学报 1987年第7期45卷 720-723页

作者：葛文正曹文娟何钰清黄维垣中国科学院上海有机化学研究所中国科学院上海有机化学研究所上海

以元素氟、高价金属氟化物和电化氟化链状有机化合物往往得到许多副产物,而主要产物产率较低,通常认为氟化时伴随有链的降解,重排和聚合等副反应.以三氟化钴进行氟化只有少量环化产物生成.近年来由于分离技术的提高,对复杂的氟化产物进... 详细信息

以元素氟、高价金属氟化物和电化氟化链状有机化合物往往得到许多副产物,而主要产物产率较低,通常认为氟化时伴随有链的降解,重排和聚合等副反应.以三氟化钴进行氟化只有少量环化产物生成.近年来由于分离技术的提高,对复杂的氟化产物进行分离鉴定、探讨氟化机理从而提高反应得率,使氟化反应进一步得到开发利用.我们将丁基苯以三氟化钻进

关键词：气相氟化 CF AB ppm 全氟丁基苯丁基环己烷

The reaction of *** radical addition to olefins initiated by single electron oxidation of perfluoroalkanesulfinate

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Chinese Journal of chemistry 1990年第4期8卷 362-369页

作者： huang, wei-yuan XIE, yuan shanghai institute of organic chemistry, academia sinica, shanghai 200032 shanghai institute of organic chemistry Academia Sinica Shanghai 200032

Sodium perfluoroalkanesulfinates [Cl(CF_2)n SO_2 Na (1), a, n=4; b, n=6; c, n=8] with the reduction potentials about 0.95-1.00V could be oxidized readily with various oxidizing agents such as Mn (OAc)_3·2H_2O, Ce(SO_4)_2, HgSO_4 and Co_2O_3 to generate perfluoroalkyl radicals which added to the olefins RCH=CHR′to give two kinds of adducts, namely RCH (R_f) CHXR′(3, X=H; 4, X=OAc), with good yields depending upon the solvent system used. Different oxidizing agents showed slight variation on the yields of the adducts. The reaction time could be greatly shortened at higher temperature. Thus, this reaction provides a new way for introducing a perfluoroalkyl group into olefinic compounds.

关键词： CF ppm CI The reaction of perfluoroalkanesulfinatesIV.Perfluoroalkyl radical addition to olefins initiated by single electron oxidation of perfluoroalkanesulfinate

Study on the synthesis of the lanthanide chelates of α-(trifluoromethyl)polyfluoroalkyl β-diketones and their application as ~1H NMR shift reagents

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Acta Chimica sinica(English Edition) 1987年第4期5卷 322-328页

作者： huang wei-yuan* ZHANG Long-Qing shanghai institute of organic chemistry,academia sinica,shanghai shanghai institute of organic chemistry Academia Sinica Shanghai

The synthesis of the lanthanide chelates of α′-（trifluoromethyl）polyfluoroalkyl β-dike-tones Ln {CF3CF2 [CF2OCF（CF2）]n COCHCOC（CH3）3}3[1,n=1;Ln=Eu（1a）,Pr（1b）,Nd（1c）,Sm（1d）,Gd（1e）,Tb（1f）,Dy（1g）,Er（1h）.2,n=2;Ln=Eu（2a）,Pr（2b）,Nd（2c）,Sm（2d）,Gd（2e）,Tb（2f）,Dy（2g）and Er（2h）] was reported and the 1H NMR shift properties were studied using alcohol,ketone,ether and amine as *** 1a,1b,2a and 2b induce shifts similar to that induced byLn（fod）3（Ln=Eu,Pr）.However compounds la and 2a are superior to Eu（fod）3,because their 1Hsignal shifts to higher field in the presence of substrate than that of Eu（fod）3 *** example,δHfor la and 2a is close to zero ppm in the presence of alcohol.A very satisfactory first order spectracan be obtained using 1a,2a,1b and 2b as 1H NMR shift reagents,1c,1f,1g,2c,2f and 2g produceupfield shifts,and 1h and 2b produce downfield shifts,1c and 2c induce shifts smaller than that of1b and 2b,whereas 1f,1g,1h,2f,2g and 2h induce very large shifts.

关键词： Study on the synthesis of the lanthanide chelates of diketones and their application as trifluoromethyl)polyfluoroalkyl NMR shift reagents