373-15-9Relevant academic research and scientific papers
Efficient SN2 fluorination of primary and secondary alkyl bromides by copper(I) fluoride complexes
Liu, Yanpin,Chen, Chaohuang,Li, Huaifeng,Huang, Kuo-Wei,Tan, Jianwei,Weng, Zhiqiang
, p. 6587 - 6592 (2013/12/04)
Copper(I) fluoride complexes ligated by phenanthroline derivatives have been synthesized and structurally characterized by X-ray crystallography. These complexes adopt as either ionic or neutral forms in the solid state, depending on the steric bulkiness of the substituent groups on the phenanthroline ligands. These complexes react with primary and secondary alkyl bromides to produce the corresponding alkyl fluorides in modest to good yields. This new method is compatible with a variety of important functional groups such as ether, thioether, amide, nitrile, methoxyl, hydroxyl, ketone, ester, and heterocycle moieties.
New modes of reactivity in the threshold of the reduction potential in solution. alkylation of lithium PAH (Polycyclic Aromatic Hydrocarbon) dianions by primary fluoroalkanes: A reaction pathway complementing the classical birch reductive alkylation
Melero, Cristobal,Herrera, Raquel P.,Guijarro, Albert,Yus, Miguel
, p. 10096 - 10107 (2008/09/17)
Some of the most highly reduced organic species in solution, such as the dianions of PAHs (polycyclic aromatic hydrocarbons) display unexpected reactivity patterns when they react with an appropriate counterpart. As seen before in their reaction with prop
Cyclization in deiodinative fluorination
Patrick, Timothy B.,Zhang, Likang
, p. 8925 - 8928 (2007/10/03)
Alkyl iodides 1-5 react with xenon difluoride with loss of iodide and incorporation of fluorine. A carbocationic intermediate undergoes cyclization with an internal olefinic function.
Mechanistic Studies of Fluorodecarboxylation with Xenon Difluoride
Patrick, Timothy B.,Khazaeli, Sadegh,Nadji, Sourena,Hering-Smith, Katy,Reif, Dirk
, p. 705 - 708 (2007/10/02)
The reaction of xenon difluoride with primary carboxylic acids involves a free-radical mechanism.Trifluoroacetic acid (1) decarboxylates in benzene to give (trifluoromethyl)benzene (2). 6-Hexenoic acid (3) produces a free radical in a radical clock reaction in which the kabs (25 deg C) for XeF2 was determined as 1.1 * 106 M-1 s-1.The primary radical from hexanoic acid was spin-trapped to give ESR signals diagnostic for the alkyl radical.Secondary acids were shown to proceed through a trivalent intermediate, but its exact nature was not proven.The acid 6 gave a rearranged product (7) characteristic of carbocations, whereas the diacid 8 gave difluoro compounds without stereoselectivity.The tertiary bicyclic acids 13 and 15 gave products only from solvent hydrogen abstraction strongly indicative of free radicals.
