408-38-8Relevant academic research and scientific papers
Reactivity study of 1,1,2,4,4,5,7,7,8,8,9,9,-tridecafluoro-5- trifluoromethyl-3,6-dioxanon-1-ene in nucleophilic reactions: Fluorination properties of secondary amine adducts
Dlouhá, Ivona,Kvi?ala, Jaroslav,Paleta, Old?ich
, p. 149 - 159 (2002)
A series of nucleophiles was reacted with (1) as a representative of perfluoro(alkyl vinyl ethers). All reactions were completely regioselective with the nucleophilic attack at the terminal carbon atom. Reactions of hydroxy compounds, thiols and sec-amines afforded addition products, but butyllithium, tributylphosphane or complex hydrides caused displacement of vinylic fluorine: butyllithium afforded cis-derivative, while reactions with hydrides and the phosphane led to mixtures of cis- and trans-derivatives. Diethylamine and piperidine adducts displayed the property to substitute hydroxyl for fluorine in hexadecan-1-ol. Molecular properties of hexafluoropropene and perfluoro(methyl vinyl ether) were calculated by ab initio method at the MP2/6-311G(d,p) level of theory and their impact on relative reactivity was estimated.
Deoxyfluorination of alcohols with aryl fluorosulfonates
Fei, Zhongbo,Hu, Jinbo,Li, Wei,Liu, Qinghe,Ni, Chuanfa,Wang, Xiu,Zhou, Min
supporting information, p. 8170 - 8173 (2021/08/23)
Aryl fluorosulfonates are developed as a deoxyfluorinating reagent in the transformation of primary and secondary alcohols into the corresponding alkyl fluorides. These reagents feature easy availability, low-cost, high stability and high efficiency. Diverse functionalities including aldehyde, ketone, ester, halogen, nitro, alkene, and alkyne are well tolerated under mild reaction conditions.
Rapid Deoxyfluorination of Alcohols with N-Tosyl-4-chlorobenzenesulfonimidoyl Fluoride (SulfoxFluor) at Room Temperature
Guo, Junkai,Kuang, Cuiwen,Rong, Jian,Li, Lingchun,Ni, Chuanfa,Hu, Jinbo
supporting information, p. 7259 - 7264 (2019/05/10)
The deoxyfluorination of alcohols is a fundamentally important approach to access alkyl fluorides, and thus the development of shelf-stable, easy-to-handle, fluorine-economical, and highly selective deoxyfluorination reagents is highly desired. This work describes the development of a crystalline compound, N-tosyl-4-chlorobenzenesulfonimidoyl fluoride (SulfoxFluor), as a novel deoxyfluorination reagent that possesses all of the aforementioned merits, which is rare in the arena of deoxyfluorination. Endowed by the multi-dimensional modulating ability of the sulfonimidoyl group, SulfoxFluor is superior to 2-pyridinesulfonyl fluoride (PyFluor) in fluorination rate, and is also superior to perfluorobutanesulfonyl fluoride (PBSF) in fluorine-economy. Its reaction with alcohols not only tolerates a wide range of functionalities including the more sterically hindered alcoholic hydroxyl groups, but also exhibits high fluorination/elimination selectivity. Because SulfoxFluor can be easily prepared from inexpensive materials and can be safely handled without special techniques, it promises to serve as a practical deoxyfluorination reagent for the synthesis of various alkyl fluorides.
Hypervalent Iodine(III)-Mediated Oxidative Fluorination of Alkylsilanes by Fluoride Ions
Xu, Peng,Wang, Feng,Fan, Guilan,Xu, Xiufang,Tang, Pingping
supporting information, p. 1101 - 1104 (2017/01/18)
The first example of a hypervalent iodine(III)-mediated oxidative fluorination of alkylsilanes by fluoride ions without the use of transition metals is demonstrated. This reaction is operationally simple, scalable, and proceeds under mild reaction conditions. Mechanistic studies suggest the involvement of a single-electron transfer resulting from the interaction of an organopentafluorosilicate and aryliodonium difluoride, which were generated in situ from the corresponding alkylsilane and iodosobenzene, respectively, in the presence of fluoride ions.
Observations on the Reaction of Xanthate Esters with 4-Methyl(difluoroiodo)benzene: a New Method for the Conversion of Alcohols to Alkyl Fluorides
Koen, Mark J.,Guyader, Frederic Le,Motherwell, William B.
, p. 1241 - 1242 (2007/10/02)
Treatment of a range of S-methyldithiocarbonates (xanthates) with 4-methyl(difluoroiodo)benzene gives the corresponding alkyl fluorides.
EASY AND EFFICIENT HETEROGENEOUS NUCLEOPHILIC FLUORINATION WITHOUT SOLVENT
Bram, Georges,Loupy, Andre,Pigeon, Philippe
, p. 1661 - 1668 (2007/10/02)
In the absence of solvent, either or were found to be effective and practical reagents for the fluorination of several organic halides under mild conditions.
Betylates. 4. The synthesis and preparative nucleophilic substitution reactions of alkyl S-betylates
King, James Frederick,Skonieczny, Stanislaw,Poole, Gary Allan
, p. 235 - 243 (2007/10/02)
Alkyl S-betylates (S,S-dialkyl-S-3propylsulfonium salts), the first examples of S-betylates (sulfonioalkanesulfonic esters), have been synthesized by two routes, and their suitability as intermediates in the transformation of alcohols by nucleophilic substitution reactions examined.They have been found to react readily in stoichiometric phase transfer processes, including substrate-reagent ion-pair reactions, like their previously studied nitrogen analogues, with the following particular features: (a) they may be used with basic nucleophiles (unlike betylates), (b) they are more simply made from commercially available starting materials than betylates, and (c) they can be made by a route that avoids a final alkylation step.
