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首页> 外文期刊>Journal of the Chemical Society, Perkin Transactions 1 >Efficient synthesis of N-(trifluoromethylsulfonyl)trifluoromethanesulfonimidoyl fluoride – the key agent in the preparation of compounds with superstrong electron-withdrawing groups and strong acidic properties
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Efficient synthesis of N-(trifluoromethylsulfonyl)trifluoromethanesulfonimidoyl fluoride – the key agent in the preparation of compounds with superstrong electron-withdrawing groups and strong acidic properties

机译：N-（三氟甲基磺酰基）三氟甲烷磺酰亚胺基氟的有效合成-制备具有超强吸电子基团和强酸性的化合物的关键试剂

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摘要

The attractive physical and chemical properties of trifluoromethanesulfonicnacid (Tf-OH) and its derivatives have led tona wealth of new compounds and applications in many fieldsnof chemistry.1 Recently, there has been a sustained interest innbis(perfluoroalkylsulfonyl)imides derivatives as Lewis acidncatalysts, fluorination reagents of aromatic compounds, electrolytesnfor lithium batteries and fuel cells, and even as bioactivenmolecules.2nWe have demonstrated with mono- and bis-N-(trifluoromethylsulfonylimino)-nsubstituted aza analogs of arenesulfonylnhalides that the replacement of the oxygen atom of sulfonylnhalides by the u0001u0001NSO2CF3 group leads to an impressive risenof the electron-withdrawing strength of these groups3 and tonuncommon reactivity of such halides.4nBis(perfluoroalkylsulfonyl)imides are the strongest acidsnknown to date. Gas phase acidity measurements have shownnthat the acidity of (CF3SO2)2NH is in excess of TfOH by 8 kcalnmolu00021 (∼6 pKa units).3b An explanation for the increased aciditynof the NH-acid compared with the OH-acid is the possiblenexistence of the tautomeric forms of (CF3SO2)2NH in which thenproton is bonded to the oxygen atom (see structure A).nExamples of this type of tautomer have been observerednwith aryl- and trialkylsilyl ethers, prepared by direct arylationnof the anion u0002N(SO2CF3)2 during pyrolysis of arenediazoniumnbis(trifluoromethylsulfonyl)amide 5 and via silylation of thenNH-acid by silanes containing bulky groups.6 However thesencompounds cannot be used as starting materials to obtain anvariety of acid A derivatives. Therefore the obtention ofnN-(trifluoromethylsulfonylimino)trifluoromethanesulfonyl halidesnand amides, as precursors to the CF3S(O)u0001u0001NSO2CF3n(Tf-aza-triflyl group) appeared highly desirable.
机译：三氟甲磺酸（Tf-OH）及其衍生物的诱人的物理和化学性质已导致在许多化学领域中产生了许多新化合物和应用。1最近，对双（全氟烷基磺酰基）酰亚胺衍生物作为路易斯酸催化剂，氟化作用一直保持着兴趣。 2n我们已经证明了单-和双-N-（三氟甲基磺酰脲基）-芳烃磺酰卤的氮杂类似物证明了u0001u0001NSO2CF3基团取代了磺酰卤的氧原子导致这些基团的吸电子强度显着提高3和此类卤化物的不寻常反应性。4nBis（全氟烷基磺酰基）酰亚胺是迄今为止已知的最强酸。气相酸度测量表明，（CF3SO2）2NH的酸度比TfOH高出8 kcalnmolu00021（〜6 pKa单位）.3b与OH酸相比，NH-酸的酸度增加的解释是（CF3SO2）2NH的互变异构形式，其中质子与氧原子键合（见结构A）.n已观察到此类互变异构体的实例包括芳基和三烷基甲硅烷基醚，它们是通过热解过程中阴离子u0002N（SO2CF3）2直接芳基化而制得的苯二氮杂双（三氟甲基磺酰基）酰胺5的合成，然后通过含有大体积基团的硅烷对NH-酸进行甲硅烷基化处理。6然而，森化合物不能用作获得各种酸A衍生物的原料。因此，非常需要获得作为CF3S（O）u0001u0001NSO2CF3n（Tf-氮杂-三氟乙炔基）的前体的nN-（三氟甲基磺酰亚胺基）三氟甲磺酰基卤化物和酰胺。

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