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5-Halo-3-oxa-perfluoropentanesulfonic acids 2,4 were obtained in high yields by treating the corresponding sulfonyl fluorides successively with KOH and concentrated H2SO4: Treatment of the acids with P2O5 gave corresponding anhydrides 3, 5. 3 reacted with various alcohols in the presence of pyridine to yield sulfonates 6. 5-Iodo-3-oxa-perfluoropentanesulfonyl fluoride (1) was converted to the acyl fluoride 9 by fuming sulfuric acid. Depending on the reaction temperature 9 can be hydrolyzed to fluorosulfonyl perfluoroalkanoic acid 10 and/or mixed dibasic acid 11. A similar phenomenon was also observed in the case of hydrolysis of fluorocarbonyl-perfluoromethanesulfonyl fluoride(13). Alcohol reacted readily with the acyl fluoride group but not with the sulfonyl group in 9 giving carboxylic esters, which can be further transformed to the corresponding sulfonates. Perfluoroalkoxide ion -O(CF2)2O(CF2)2SO2F prepared from 9 and F- reacted with active alkyl halides yielding the corresponding ethers. The interaction of 5-halo-3-oxa-perfluoroalkane-sulfonyl fluoride with AlCl3 was investigated. Friedel-crafts acylation of aromatic compounds with 9 in the presence of anhydrous AlCl3 is also reported. The yields of the desired ketones can be improved by using CCl4 as a solvent and changing the order of addition of reactants. 相似文献
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本文研究了X(CF~2)~nI(X=H, F,Cl,Br,I),I(CF~2)~2O(CF~2)~2SO~2NEt~2,R~pCF~2Br,Br(CF~2)~2O(CF~2)~2SO~2NEt~2与PhSNa的S~[RN]1反应.这个反应不仅易于发生,而且苯基硫酚阴离子单取代产物或二取代产物的产率较高.苯基硫酚阴离子与ω-H,ω-Cl全氟烷羟并不发生反应.Cl~2CYCF~2O(CF~2)~2SO~2NEt~2(Y-Cl,F)也易于PhSNa反应,并且还发生C-O断裂得PhSCF~2-CYClH,PhSCF~2CYCl~2,PhSCF=CYCl和(PhS)~2C=C(SPh)~2,PhSCOCF~2SO~2NEt~2,估计反应是通过阴离子型链式机理. 相似文献
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5-卤-3-氧杂-全氟戊磺酰氟(1)依次用苛性钾、浓硫酸和五氧化二磷处理可顺利地得到相应的磺酸和磺酸酐.在吡啶存在下,[I(CF_2)_2O(CF_2)_2SO_2]_2O(3)与醇反应得磺酸酯(6).1在发烟硫酸作用下,可转化成酰氟9.随着反应温度的不同,9水解为酸10和/或二元酸11.氟羰基全氟甲磺酰氟的水解也有类似现象.醇与9的酰氟基反应得羧酸酯,而不与磺酰氟基反应.但可进一步转化为磺酸酯.由9与F~-生成的全氟烷氧基阴离子-O(CF_2)_2O(CF_2)_2SO_2F与活泼的卤代烷作用得醚.还研究了5-卤-3-氧杂-全氟戊磺酰氟与三氯化铝的作用,在无水三氯化铝存在下对9进行了芳烃的Friedel-Crafts酰基化,以四氯化碳为溶剂并改变加料顺序,可提高酮的产率. 相似文献
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以3-氧杂多氟烷烃磺酰氟XOCF2CF2SO2F为原料,在二氯甲烷中于-20~-30℃与三乙胺、含氟醇或苯酚反应得到一系列氧杂多氟磺酸酯XOCF2CF2SO3R(1a~1g),产率52~90%.影响产率的主要因素是反应温度,而不是碱用量.亲核试剂与这些磺酸酯作用,主要引起酯基的C—O断裂.如1a或1c与I,CNS和R1R2NH反应得HCF2CF2CH2Y(Y=I,CNS,R1R2N),与HCF2CF2CH2θ得对称醚(HCF2CF2CH2)2O. 相似文献
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本文研究了X(CF_2)_nI(X=H,F,Cl,Br,I),I(CF_2)_2O(CF_2)_2SO_2NEt_2,R_1CF_2Br,Br(CF_2)_2O(CF_2)_2SO_2NEt_2与PhSNa的S_(RN)l反应。这个反应不仅易于发生,而且苯基硫酚阴离子单取代产物或二取代产物的产率较高。苯基硫酚阴离子与ω-H,ω-Cl全氟烷羟并不发生反应。Cl_2CYCF_2O(CF_2)_2SO_2NEt_2(Y=Cl,F)也易与PhSNa反应,并且还发生C—O断裂得PhSCF_2-CYClH、PhSCF_2CYCl_2、PhSCF—CYCl和(PhS)_2C—C(SPh)_2,PhSCOCF_2SO_2NEt_2,估计反应是通过阴离子型链式机理。 相似文献
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