Ethers as solvents

Ethers such as diethyl ether dissolve a wide range of polar and nonpolar organic compounds. Nonpolar compounds are generally more soluble in diethyl ether than alcohols because ethers do not have a hydrogen bonding network that must be broken up to dissolve the solute. Because diethyl ether has a moderate dipole moment, polar substances dissolve readily in it. 

The lone pair electrons of an ether also stabilize electron deficient species such as BF3 and borane (BH3). For example, the borane-THF complex is used in the hydroboration of alkenes (Section 15.8). 

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In 1932 a class of complexes consisting of ethers, sodium, and polycycHc hydrocarbons was discovered (19). Sodium reacts with naphthalene in dimethyl ether as solvent to form a soluble, dark-green, reactive complex. The solution is electrically conductive. The reaction has been described as follows... 

Treatment of thiiranes with lithium aluminum hydride gives a thiolate ion formed by attack of hydride ion on the least hindered carbon atoms (76RCR25), The mechanism is 5n2, inversion occurring at the site of attack. Polymerization initiated by the thiolate ion is a side reaction and may even be the predominant reaction, e.g. with 2-phenoxymethylthiirane. Use of THF instead of ether as solvent is said to favor polymerization. Tetrahydroborates do not reduce the thiirane ring under mild conditions and can be used to reduce other functional groups in the presence of the episulfide. Sodium in ammonia reduces norbornene episulfide to the exo thiol. 

The present method offers several advantages over earlier methods. The use of carbon tetrachloride instead of diethyl ether as solvent avoids the intrusion of certain radical-chain reactions with solvent which are observed with bromine and to a lesser degree with chlorine. In addition, the potassium bromide has a reduced solubility in carbon tetrachloride compared to diethyl ether, thus providing additional driving force for the reaction and ease of purification of product. The selection of bro-... 

The treatment of ketoximes with lithium aluminum hydride is usually a facile method for the conversion of ketones into primary amines, although in certain cases secondary amine side products are also obtained. Application of this reaction to steroidal ketoximes, by using lithium aluminum deuteride and anhydrous ether as solvent, leads to epimeric mixtures of monodeuterated primary amines the ratio of the epimers depends on the position of the oxime function. An illustrative example is the preparation of the 3(x-dj- and 3j5-di-aminoandrostane epimers (113 and 114, R = H) in isotopic purities equal to that of the reagent. 

BU2AIH, CH2CI2, -78°, 95% yield. /-BU2AIH, CH2CI2, toluene, 84% yield. Three pivaloates were cleaved from a zaragozic acid intermediate. The use of THE or ether as solvent failed to remove all three. 

Following the procedure given above, cyclopropylidenecyclopentane is prepared in 85% yield from 34.4 g (0.09 mole) of the phosphonium salt, 3.83 g (0.097 mole) of sodium amide (used instead of phenyllithium), and 8.4 g (0.1 mole) of cyclopentanone in ether as solvent (350 ml). The product has bp 69-70770 mm. 

Ketene di(2-melhoxyethyl) acetal has been obtained by the present method with the use of diethylene glycol dimethyl ether as solvent.3 Other methods for the preparation of ketene acetals include the dehydrohalogenation of a halo acetal with potassium t-butoxide 4 and the reaction of an a-bromo orthoester with metallic sodium.5... 

We investigated lipase-catalyzed acylation of 1-phenylethanol in the presence of various additives, in particular an E. additive using diisopropyl ether as solvent. Enhanced enantioselectivity was obtained when a BEG-hased novel IE, i.e., imidazolium polyoxyethylene(lO) cetyl sulfate, was added at 3-10 mol% vs. substrate in the Burkholderia cepacia lipase (hpase PS-C) catalyzed transesterification using vinyl acetate in diisopropyl ether or a hexane solvent system. ... 

Such a dispersant formulation for dispersing oil contains a mixture of a sorbitan monoester of an aliphatic monocarboxylic acid, a polyoxyethylene adduct of a sorbitant monoester of an aliphatic monocarboxylic acid, a water-dispersible salt of a dialkyl sulfosuccinate, a polyoxyethylene adduct of a sorbitan triester or a sorbital hexaester of an aliphatic monocarboxylic acid, and a propylene glycol ether as solvent [311,312]. 

A-Acylimidazoles are easily reduced to the corresponding aldehydes with LiAlH4 in THF or ether as solvent.[1] Thus, aliphatic, conjugated aliphatic, aromatic, conjugated aromatic, and heteroaromatic aldehydes can all be obtained in this way in moderate to high yields. 

An explosive red/orange solid, obtained from dirhenium heptoxide and hydrogen peroxide reacting in ether as solvent. 

Thus far, a-glucopyranoside formation has not been extensively investigated (67) because this connection is less frequently found in glycoconju-gates. However, it was observed that, with / -trichloroacetimidate la-/ as donor, stronger catalyst systems, as for instance Me3SiOTf, favor formation of the thermodynamically more-stable product, especially when the reactions are performed in ethers as solvents (Table III reactions with 3 A, 2G, and 2F) (67). 

Thus the reaction site, the double bond, participates in the charge and polymerization can take place. That the vinyl group conjugated with the oxygen atom is more basic than an ordinary ether oxygen is shown by the fact that alkyl vinyl ethers can be polymerised readily in dialkyl ethers as solvents. 

SnC>2 nanoparticles have been successfully synthesized by chemical co-precipitation method using ethanol, acetone, tetrahydrofuran (THF) and ether as solvents. X-ray Diffraction (XRD), Field Emission Electron Microscopy (FESEM) and Transmission Electron Microscopy (TEM) have been used to study the crystallographic and morphological properties of synthesized SnC>2 nanoparticles, while their optical properties have been studied by UV-Visible absorption spectroscopy. UV-Vis absorption spectra shows a weak quantum confinement in all the synthesized SnCL samples. The photo-catalytic activity of as-synthesized SnC>2 nanoparticles under UV irradiation has been evaluated using Methylene Blue (MB) dye as a test contaminant in water. The results showed that solvents played a key role to control the morphology and photo-catalytic activity of SnCE nanoparticles. 

Endo et al. investigated the reductive decomposition of various electrolytes on graphite anode materials by electron spin resonance (ESR). In all of the electrolyte compositions investigated, which included LiC104, LiBF4, and LiPFe as salts and PC, DMC, and other esters or ethers as solvents, the solvent-related radical species, which were considered to be the intermediates of reductive decomposition, were detected only after prolonged cathodic electrolysis. With the aid of molecular orbital calculation, they found that the reduction of salt anion species is very difficult, as indicated by their positive reduction enthalpy and that of free solvent (A/4 — 1 kcal mol ). However, the coordination of lithium ions with these solvents dramatically reduces the corresponding reduction enthalpy (A/ —10 kcal mol ) and renders the reaction thermodynamically favored. In other words, if no kinetic factors were to be considered, the SEI formed on carbonaceous anodes... 

It was observed that in the case of bromo- or iodo-substituted benzyhc tellurides the lithium-Br exchange and/or the halogen displacement by the n-butylhthinm competes with the Te-Li exchange, resulting in lower yields of the desired products. This drawback is avoided by using ether as solvent. 

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