78710-81-3Relevant academic research and scientific papers
Quaternary Ammonium Trifluoromethoxide Salts as Stable Sources of Nucleophilic OCF3
Britton, Robert,Friesen, Chadron M.,Jelier, Benson J.,Martin, Rainer E.,Meanwell, Michael,Newton, Josiah J.
, p. 1785 - 1790 (2020/03/24)
The reaction of nucleophilic tertiary amines with trifluoromethyl and pentafluoroethyl methyl ethers provides quaternary ammonium trifluoromethoxide (NR4OCF3) and pentafluoroethoxide (NR4OCF2CF3) salts, respectively, in good yields. The new trifluoromethoxide salts disclosed herein are uniquely stable for extended periods of time in both the solid state and in solution, which complements contemporary reagents. Here we describe the preparation of a range of NR4OCF3 salts, their long-term stability, and utility in substitution reactions.
Synthesis of α-Cyano and α-Sulfonyl Cyclic Ethers via Intramolecular Reactions of Peroxides with Sulfone- And Nitrile-Stabilized Carbanions
Horn, Alissa,Dussault, Patrick H.
, p. 14611 - 14626 (2019/11/13)
The intramolecular reaction of carbon nucleophiles with oxygen-centered electrophiles has been little explored outside of nucleophilic epoxidation. We now report the synthesis of sulfonyl- and cyano-substituted oxacycles via intramolecular reaction of sul
Preparation of Some Novel Butyl, Butenyl, Butadienyl and Bytynyl Sulfone Electrophiles for Use in Enolate Trapping Studies
Loughlin, Wendy A.,Haynes, Richard K.
, p. 651 - 662 (2007/10/02)
The preparation of some novel four-carbon electrophiles and electrophile intermediates is described.Thus, the chlorobutenyl sulfone (5), the iodobutynyl sulfone (6) and the hitherto unreported chlorobutynyl sulfone (4) were prepared.The novel intermediates, containing a chelating imidazolyl functionality, the N-methylimidazolyl sulfides (13)-(15) were also prepared.However, they polymerized rapidly, thus preventing further synthetic manipulations.The preparation of the α-(trimethylsilyl)butadienyl sulfones (17) and (18) is described and the mode of formation of the intermediate α-trimethylsilyl sulfides (21) and (22) from the trimethylsilylbutenyl sulfide (27) is discussed.
γ- and δ-epoxy sulfones. Formation of different ring-sized products upon reaction with CH3MgI or LiN2
Decesare, John M.,Corbel, Bernard,Durst, Tony,Blount, John F.
, p. 1415 - 1424 (2007/10/02)
γ-Epoxy sulfones in which the epoxide function is terminal yield cyclopropylmethanol derivatives on reaction with methylithium or lithium diisopropylamide.In contrast, treatment of these epoxides with two equivalents of CH3MgI gives only cis-3-phenylsulfonylcyclobutanols.The cis-relationship between the OH and sulfonyl groups was proven in one instance by an X-ray stucture determination.Inernal γ-epoxy sulfones yield cyclopropylmethanols with all bases studied.All δ-epoxy sulfones studied furnished cis-3-phenylsulfonylcyclopentanols upon reaction with the Grignard reagent.These same epoxides gave either cyclopentanols or noncyclic products upon reaction with LDA; no cyclobutane ring containing products were obtained contrary to the expectations based on Stork's results with the corresponding epoxy nitriles (ref. 2).The mechanism of the Grignard-mediated reaction involves epoxide opening by iodide ion, α-sulfonyl Grignard formation, and, finally, cyclization.When LDA or CH3Li is used the products are formed by an intramolecular SN2 opening of the epoxide by an α-lithio sulfone.
