Hydrogen Fluoride Salts Research Articles

Use of Task-Specific Ionic Liquid for Selective Electrocatalytic Fluorination

Highly selective indirect anodic fluorination of organic compounds was successfully carried out for the first time by using a task-specific ionic liquid of iodoarene as a mediator in ionic liquid hydrogen fluoride salts.

ChemInform Abstract: Prins Cyclization in Ionic Liquid Hydrogen Fluoride Salts: Facile and Highly Efficient Synthesis of 4‐Fluorinated Tetrahydropyrans, Thiacyclohexanes, and Piperidines.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Prins Cyclization in Ionic Liquid Hydrogen Fluoride Salts: Facile and Highly Efficient Synthesis of 4‐Fluorinated Tetrahydropyrans, Thiacyclohexanes, and Piperidines

AbstractPrins cyclization of homoallylic alcohols with various aldehydes was investigated in ionic liquid hydrogen fluoride (HF) salts, which played roles as a reaction medium, a catalyst, and a fluorine source. The reaction afforded the corresponding 4‐fluorinated tetrahydropyrans in excellent yields with a high stereoselectivity (cis form exclusively). When benzaldehydes having a strongly electron‐donating group at the para position were used, the stereoselectivity was lost in this system. In order to apply this method to the synthesis of other 4‐fluorinated heterocyclic compounds, we also carried out thia‐Prins and aza‐Prins cyclization in HF salt and successfully obtained 4‐fluorinated thiacyclohexanes and piperidines, respectively.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

ChemInform Abstract: Facile and Highly Efficient Synthesis of Fluorinated Heterocycles via Prins Cyclization in Ionic Liquid Hydrogen Fluoride Salts

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Anodic Fluorination and Fluorodesulfurization in Ionic Liquid Hydrogen Fluoride Salts with Polyether Additives

In order to avoid an anodic passivation, which sometimes occurs during anodic fluorination in organic solvent, we carried out anodic fluorination and fluorodesulfurization of sulfur-containing compounds in neat ionic liquid hydrogen fluoride salts (, , ). The addition of polyether additives into the reaction system highly improved the yields of the desired fluorinated products due to their anodic stability and coordination ability to counter cations of fluoride ions. Furthermore, HF salts allow the electrolysis in a large current density and exhibited a good result, especially in the presence of polyether additives.

Effects of additives on anodic fluorination in ionic liquid hydrogen fluoride salts

Anodic fluorination of ethyl α-(2-pyrimidylthio)acetate in neat ionic liquid hydrogen fluoride salts (Et 3N–3HF, Et 4NF–4HF, Et 4NF–5HF) was investigated to avoid an anode passivation, which sometimes occurs during anodic fluorination in organic solvent. In order to improve the yield of fluorinated product, polyether having coordination ability to cation and anodic stability was introduced to the reaction system as additives (∼3%). Furthermore, such additives were found to be also effective for anodic fluorodesulfurization of 4-phenylthio-1,3-dioxolan-2-one in neat ionic liquid system.

Facile and highly efficient synthesis of fluorinated heterocycles via Prins cyclization in ionic liquid hydrogen fluoride salts

Prins cyclization of homoallylic alcohols, thiols, and amines with various aldehydes in an ionic liquid HF salt (Et(4)NF.5HF) afforded the corresponding 4-fluorinated heterocycles in excellent yields.

IMPORTANCE OF AMINE HYDROHALIDES IN ALCOHOLYSIS OF PHOSPHOROUS ACID AMIDES

Abstract The data are presented on the rates of deuteromethanolysis of 2-fluoro-1,3,2-dioxaphosphorinane 1 in the presence of various bases differing in the basicity and of that of 2-amino-1,3,2-dioxaphosphorinanes 2–4 catalysed by hydrogen fluoride salts of different amines. The alcoholysis of the fluorophosphite 1 in the presence of imidazole, N-ethylaniline and 2,6-di-tert-butyl-4-methylpyridine proceeds slowly whereas alcoholysis of the amidoesters 3,4 catalysed by imidazole and N-ethylaniline hydrofluorides occurs rapidly even at room temperature. These data do not match the hypothesis that halophosphites are intermediates in the alcoholysis of amidophosphites in the presence of amine hydrohalides.