Isothiouronium salts as useful and odorless intermediates for the synthesis of thiaalkylimidazolium ionic liquids

Matiello, Gabriela Inês; Pazini, Alessandra; Silva, Kácris I.M. da; Costa, Rafaela Gomes Martins da; Ebeling, Günter; Dupont, Jaı̈rton; Limberger, Jones; Scholten, Jackson D.

doi:10.1016/j.tetlet.2019.02.013

Cited by 4 publications

(1 citation statement)

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“…An example of thiol functionalization of the anion has also been reported and these ILs’ systems have been studied as enhancers of nanotube dispersion in a rubber matrix [17]. Recently, a new access to thioalkylimidazolium ILs exploiting odorless intermediates and their use as ligands in Ullmann and Suzuki couplings have been reported [18]. As part of an ongoing project aimed at identifying ILs characterized by switching properties, the preparation of new thiol-functionalized carboxylate ILs is described.…”

Section: Introductionmentioning

confidence: 99%

Unexpected Intrinsic Lability of Thiol-Functionalized Carboxylate Imidazolium Ionic Liquids

et al. 2019

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New thiol-functionalized carboxylate ionic liquids (ILs), varying both for the cation and for the anion structures, have been prepared as new potential redox switching systems by reacting either 3-mercapto propionic acid (3-MPA) or N-acetyl-cysteine (NAC) with commercially available methyl carbonate ILs. Different ratios of thiol/disulfide ILs were obtained depending both on the acid employed in the neutralization reaction and on the reaction conditions used. Surprisingly, the imidazolium ILs displayed limited thermal stability which resulted in the formation of an imidazole 2-thione and a new sulfide ionic liquid. Conversely, the formation of the imidazole 2-thione was not observed when phosphonium disulfide ILs were heated, thus confirming the involvement of the imidazolium ring in an unexpected side reaction. An insight into the mechanism of the decomposition has been provided by means of DFT calculations.

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Section: Introductionmentioning

confidence: 99%