Selective, Electrophilic Fluorinations Using N-Fluoro-o-benzenedisulfonimide was written by Davis, Franklin A.;Han, Wei;Murphy, Christopher K.. And the article was included in Journal of Organic Chemistry in 1995.Reference of 56619-93-3 This article mentions the following:
The synthesis of N-fluoro-o-benzenedisulfonimide (NFOBS) and its use as an electrophilic fluorinating reagent with nucleophilic substrates is described and compared with that of N-fluorobenzenesulfonimide (NFSi). NFOBS is prepared in three steps in 81% overall yield from com. available o-benzenedisulfonic acid and involves treatment of o-benzenedisulfonimide with dilute fluorine (10% F2/N2). Reaction of NFOBS with metal enolates, silyl enol ethers, and 1,3-dicarbonyl compounds affords the corresponding α-fluoro compounds in yields up to 95%, with good control of mono- and difluorination. Fluorination of ortho-metalated aromatic compounds was achieved in modest to good yields (10-80%). While the reactivities of NFOBS and NFSi are similar, better yields were observed with the former reagent in the fluorination of metal enolates, Grignard and lithium reagents, while NFSi gave better results with the ortho-lithiated aromatic substrates. The available evidence suggests an SN2-type mechanism for the fluorination of nucleophilic substrates by these reagents. In the experiment, the researchers used many compounds, for example, N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3Reference of 56619-93-3).
N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3) belongs to ethers. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapours of certain ethers are used as insecticides, miticides, and fumigants for soil. Ethers are good solvents partly because they are not very reactive. Most ethers can be cleaved, however, by hydrobromic acid (HBr) to give alkyl bromides or by hydroiodic acid (HI) to give alkyl iodides.Reference of 56619-93-3
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem