Fluorinated macrocyclic ethers as fluoride ion hosts. Novel structures and dynamic properties

Azoles as Reactive Nucleophiles with Cyclic Perfluoroalkenes

“…Over the last half century, acyclic or cyclic fluorinated olefinic compounds have been of considerable interest [1] because of the presence of the reactive vinylic fluorine atoms, which provides an easy route for the introduction of a wide variety of functional groups ranging from alkoxides, [2,3] phenoxides, [4,5] primary or secondary amines, [6] sulfanyls, [7] lithium salts, [8] and carbon [9] to phosphorus-bonded groups. [10] Various synthetic methods including free radical addition, [11] electrophilic, [12] and nucleophilic [2][3][4][5][6][7][8][9][10] substitution have been employed for the introduction of these groups.…”

“…[10] Various synthetic methods including free radical addition, [11] electrophilic, [12] and nucleophilic [2][3][4][5][6][7][8][9][10] substitution have been employed for the introduction of these groups. Among these methods, nucleophilic substitution of fluoroalkenes, which involves addition followed by b-elimination in the presence of a base, is a well-established strategy.…”

“…Among these methods, nucleophilic substitution of fluoroalkenes, which involves addition followed by b-elimination in the presence of a base, is a well-established strategy. Substitutions of fluoroaromatic, [13] fluoroheterocyclic, [14] fluoroalkene, [2][3][4][5][6][7][8][9][10]12] and, more recently, fluorinated fullerenes [15] are being used to carefully design compounds with desired physical and chemical properties. This enables their use in diverse applications, [4,16] such as blood substitutes, agrochemicals, electric insulators, liquid-crystalline materials, conducting polymers, the construction of super hydrophobic surfaces, and so forth.…”

“…[3] Recently, substitutions of perfluorocyclopentene have been used successfully in fabricating photochromic dithiazolylethene-based derivatives, which find application in many optoelectronic devices. [17] Perfluorinated olefins are a good source for generating reactive carbanions, which can be used to make stable isolable salts.…”

“…[18] They also form stable coordination complexes with metal ions. [19] Typically, mono-or disubstituted products [2][3][4][5][6][7][8][9][10] are formed in which either one or both of the vinylic fluorine atoms is substituted depending upon the nucleophilicity of the reagent. However, in the case of some bifunctional nucleophiles, [5,20] it was observed that occasionally not only vinylic but also allylic fluorine atoms may be substituted to yield trisubstituted compounds.…”