Alkyl Phenyl Ethers Research Articles

Ion-radical complexes in the gas phase: structure and mechanism in the fragmentation of ionized alkyl phenyl ethers

Ion-radical complexes in the gas phase: structure and mechanism in the fragmentation of ionized alkyl phenyl ethers

New Oxidative Aromatization of α,β-Unsaturated Cyclohexenones with Iodine–Cerium(IV) Ammonium Nitrate in Alcohol

Abstract The reaction of 2-cyclohexen-1-one derivatives with iodine–cerium(IV) ammonium nitrate in alcohols (methanol, ethanol, 1-propanol, 2-propanol, and 1-butanol) under refluxing, gave the corresponding alkyl phenyl ethers in good yields. In the case of diol (ethylene glycol, 1,3-propanediol, and 1,4-butanediol), phenoxyalkanol derivatives were obtained. The present method was also applicable to oxidative rearrangement of isophorone.

Insect juvenile hormone mimetic activity of (4-substituted)phenoxyalkyl compounds with various nitrogenous and oxygenous functions and its relationship to their electrostatic and stereochemical properties

We prepared classes of insect juvenile hormone (JH) mimetic compounds in which oxime, hydroxylamine, ester, amide, carbamate, and urea were built in at the alkane moiety of the 4-substituted phenyl alkyl ether structure. Some of them had effects on Culex pipiens as strong as those of the most active JH mimetics known. Calculation of the electrostatic potentials and stereochemical interpretations showed that the most active compond of each class was the entity in which the function in question was incorporated so that its negative potential peak about 4.6 A distant from the molecular edge within the framework of the receptor model drawn previously by us (...)

Charge transfer induced nematic columnar phase in low molecular weight disc-like systems [1

Abstract Two large pentakis(phenylethynyl)phenyl alkyl ethers, without side chains as is usual for discotic systems, were synthesized in palladium catalysed one pot coupling reactions. These low molecular weight and non-liquid-crystalline electron donor compounds were doped with 2,4,7-trinitrofluorenone under the formation of charge transfer complexes. The induction of two types of enantiotropic mesophases (i.e. nematic and hexagonal columnar phases (Nc and Dho)) was observed. These charge transfer-induced mesophases were characterized by polarization microscopy, differential scanning calorimetry, and X-ray analysis; phase diagrams of the binary systems were also recorded as well as the hexagonal columnar to nematic columnar transition as a function of the length of the disturbing alkoxy group. It is considered possible now to study low molecular mass Nc phases by tailor-made two component mixtures on the basis of our easily accessible disc-shaped multiynes.

Ion‐Neutral complexes from protonated propyl phenyl ethers. Gas‐phase solvolysis versus elimination‐readdition

AbstractIon‐neutral complexes, well attested as intermediates in the expulsion of alkenes from M+⋅ and MH+ ions from primary alkyl phenyl ethers, are shown to intervene in the decomposition of the MH+ ion of a secondary alkyl phenyl ether, (CD3)2CHOPh. Chemical ionization (CI) (methane reagent gas)‐mass‐analysed ion kinetic energy spectroscopy (MIKES) shows ions of both m/z 96 and 97, indicating that the proton deposited by the CI reagent exchanges with the methyl deuterium atoms. The ratio of daughter ion intensities, as well as the proportions of ions of m/z 95, 96 and 97 from the MH+ of CD3CH2CD2OPh, agree with predictions based on the gas‐phase solvolysis mechanism, in which [i‐Pr+ PhOH] complexes form from the protonated parent via simple bond heterolysis. An alternative mechanism, elimination‐readdition, would proceed via [propene PhOHD+] complexes. This latter mechanism predicts a ratio of daughter ion intensities that is very different from gas‐phase solvolysis and which disagrees with experiment. The elimination‐readdition pathway is effectively ruled out, while the gas‐phase solvolysis mechanism is reinforced.

Preparation of Phenylalkyl Ethers and Phenyl Esters from Benzenediazonium Tetrafluoroborate with Alkoxytrimethylsilanes and Trimethylsilyl Esters

Sonication assisted reaction of benzenediazonium tetrafluoroborate with alkoxytrimethylsilanes and trimethylsilyl esters gives phenylalkyl ethers and phenyl esters, respectively, with trialkyl-(aryl) borates as byproducts. The scope of the reaction, experimental conditions and proposed mechanism are discussed.

ChemInform Abstract: Thermal Decomposition of Phenyl Alkyl Ethers.

AbstractReaction products and intermediates of the thermal conversions (600‐1200 °C; ca. 120 mPa) of (I)‐(III) are determined.

ChemInform Abstract: Monohalogenation of Alkyl Phenyl Ethers (I) in Micellar and Vesicular Media.

ChemInform Abstract: Monohalogenation of Alkyl Phenyl Ethers (I) in Micellar and Vesicular Media.

Monohalogenation of alkyl phenyl ethers in micellar and vesicular media

On determine les constantes de vitesse et la regioselectivite de la monohalogenation de C 6 H 5 OR (R=C 5 H 11 , C 9 H 19 , C 12 H 25 ) par le chlore et le brome aqueux dans des solutions micellaires de (dodecyl)sulfate de sodium et des solutions vesiculaires de ([diheptadecyl-2,2 dioxolanne-1,3yl-4methoxy]-3) propanesulfonate-1 de sodium et de dl-α-dipalmitoylphosphatidylcholine

The fragmentation of ionized alkyl phenyl ethers

AbstractThe energetics of olefin loss from ionized alkyl phenyl ethers have been determined by ionization and appearance energy measurements. It is concluded that the reaction is governed by one or more of three features: (i) the strength of the bond between the phenoxy radical and the alkyl ion; (ii) the ease of isomerization of the alkyl ions, chiefly by H‐shifts therein, and (iii) the strength of the CH bond (primary, secondary and tertiary) involved in the H transfer to oxygen which precedes the olefin loss. The possible participation in the reaction of distonic ions and proton bound radical‐molecule pairs is also discussed.

ChemInform Abstract: Substitution of a Hydrogen Atom in 6‐Oxo‐6H‐anthra(1,9‐cd)isoxazoles by Alkyl Phenyl Ethers and Alkylbenzenes.

AbstractIn the presence of the Lewis acid AlCl3 the reaction between the 3‐bromoisoxazoloanthrone (I) specified in the title and the phenol ethers (II) or the alkylbenzenes (V) proceeds regiospecifically at position C(5) to give the 5‐aryl derivatives (III) or (VI) as the result of substitution of hydrogen.

ChemInform Abstract: Synthetic Application of Micellar Catalysis. Williamson′s Synthesis of Ethers.

Abstract A simple, rapid and efficient procedure for the preparation of di-alkyl, simple phenyl-alkyi and hindered phenyl-alkyi ethers has been developed. Based on the principle of micellar catalysis the method involves alkylation of the alkoxide or the phenoxide ion with an alkyi chloride at 80°C in the presence of cationic micelles. For the preparation of phenyl-alkyl ethers normal micelles were used, while for the di-alkyl ethers reverse micelles were more effective. By increasing the ionic strength of the solution the rate of formation of phenyl-alkyl ethers could be increased.

Thermal Decomposition of Phenyl Alkyl Ethers

AbstractReaction products and intermediates of the thermal conversions (temperature range: 600 to 1200°C, total pressure about 120 mPa) of phenyl methyl ether (1), phenyl ethyl ether (2), and m‐cresyl methyl ether (3) were determined in a pyrolysis apparatur set combined with mass spectral „real time”︁ analysis. In all cases, the predominant initial process was PhO–R bond homolysis. Phenoxy type radicals thus generated decompose unimolecularly to cyclopentadienyl type radicals and carbon monoxide. In runs with 1 and 2 cyclopentadienyl dimers (C10H10) were formed and, in addition, at temperatures >1000°C, naphthalene (C10H8). Under similar conditions the m‐methylphenoxy radical (from 3) suffers CO elimination providing the methylcyclopentadienyl radical which chiefly gives benzene instead of the dimers or the products derived from it. Under the applied conditions only bimolecular stabilization of the unsubstituted cyclopentadienyl radical proved possible, whereas the methyl substituted radical has a chance for unimolecular stabilization, too, as a result of which fulvene is formed through the loss of hydrogen. Fulvene is a direct benzene precursor.

Extractions and reactions of coals below 100 °C: 2. Reactions of the toluene-insoluble, pyridine-soluble fraction of Illinois No. 6 coal

The toluene-insoluble, pyridine-soluble (TIPS) fractions of an Illinois No. 6 coal were investigated as a model for the insoluble portion of coal. Various TIPS fractions had number-average molecular weights ( M ̄ n ) in pyridine of 9080 to 1380. These fractions were treated with a variety of reagents known to cleave ester and ether bonds. The abilities of these reagents were measured by decrease in M ̄ n of the TIPS products. The order was found to be: ZnCl 2> LiI · H 2 O > pyridine · HI > benzylamine > alcoholic KOH > toluene sulphonic acid. Ester groups were determined from saponification equivalents and the effects of alcoholic KOH. Evidence for ethers came from effects of amines, HI and sodium on the M ̄ n . HI appears to cleave more bonds and more phenyl alkyl and benzyl ether than dialkyl ether bonds.

Synthetic application of micellar catalysis. williamson's synthesis of ethers

A simple, rapid and efficient procedure for the preparation of di-alkyl, simple phenyl-alkyi and hindered phenyl-alkyi ethers has been developed. Based on the principle of micellar catalysis the method involves alkylation of the alkoxide or the phenoxide ion with an alkyi chloride at 80°C in the presence of cationic micelles. For the preparation of phenyl-alkyl ethers normal micelles were used, while for the di-alkyl ethers reverse micelles were more effective. By increasing the ionic strength of the solution the rate of formation of phenyl-alkyl ethers could be increased.

Alkyl phenyl ether radical cations in the gas phase: A reaction model

Organic Mass SpectrometryVolume 22, Issue 11 p. 746-747 OMS Letter Alkyl phenyl ether radical cations in the gas phase: A reaction model G. Sozzi, G. Sozzi Département de Chimie, Ecole Polytechnique, 91128 Palaiseau Cedex, FranceSearch for more papers by this authorH. E. Audier, H. E. Audier Département de Chimie, Ecole Polytechnique, 91128 Palaiseau Cedex, FranceSearch for more papers by this authorP. Mourgues, P. Mourgues Département de Chimie, Ecole Polytechnique, 91128 Palaiseau Cedex, FranceSearch for more papers by this authorA. Millet, A. Millet Département de Chimie, Ecole Polytechnique, 91128 Palaiseau Cedex, FranceSearch for more papers by this author G. Sozzi, G. Sozzi Département de Chimie, Ecole Polytechnique, 91128 Palaiseau Cedex, FranceSearch for more papers by this authorH. E. Audier, H. E. Audier Département de Chimie, Ecole Polytechnique, 91128 Palaiseau Cedex, FranceSearch for more papers by this authorP. Mourgues, P. Mourgues Département de Chimie, Ecole Polytechnique, 91128 Palaiseau Cedex, FranceSearch for more papers by this authorA. Millet, A. Millet Département de Chimie, Ecole Polytechnique, 91128 Palaiseau Cedex, FranceSearch for more papers by this author First published: November 1987 https://doi.org/10.1002/oms.1210221111Citations: 30AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article.Citing Literature Volume22, Issue11November 1987Pages 746-747 RelatedInformation

ChemInform Abstract: Reactions of 6H‐6‐Oxoanthra(1,9‐cd)isoxazoles with Alkylphenyl Ethers and Dimethylaniline.

AbstractThe reactions between the anthra(1,9‐cd)isoxazoles (I) or (V) and the phenyalkyl ethers (II) or N,N‐dimethylaniline are studied for the first time.

Selectivity of aromatic chlorination reactions within a reversed-phase liquid chromatography column

Substrate selectivity was obtained in the chlorination of a series of n -alkyl phenyl ethers by chlorine water on a reversed-phase high performance liquid chromatography column at 25°C.

Effect of the molecular weight of poly(ethylene glycol), used for the surface treatment of calcium carbonate, on the tensile modulus of filled oriented polypropylene

AbstractA relation between tensile modulus of oriented polypropylene filled with calcium carbonate, and modified with poly(ethylene glycol) (PEG) or alkyl phenyl ether derivatives (APED) of different molecular weights was investigated. Upon stressing, voids appear in the composites material. For systems prepared with unmodified CaCO3, the void volume increases with an increase of filler content. For systems containing modified CaCO3, the void volume is smaller than the one of the reference material and decreases with an increase of PEG or APED molecular weights (which range from 400 to 4000 for PEG). Moreover, the relative modulus of oriented composites, Edc/Edr, are reasonably accounted by the void volume irrespective of filler content and modifier molecular weight, wherein Edc, Edr are respectively the modulus of oriented composites and the modulus of oriented polymer matrix.

Study of conjugation effects by NMR spectroscopy. XXIV. Determination of the conformational composition of alkyl phenyl ethers with branched alkyl radicals from the13C-1H and13C-13C spin-spin coupling constants

During analysis of the13C-1-H and13C-13C spin-spin coupling constants of the phenyl group in alkyl phenyl ethers it was established that the steric inhibition of the conjugation due to increase in the branching of the alkyl group partial in nature and is strongest in 2-methyl-2-phenoxypropane, whereas further increase in the effective volume of the alkyl group leads to some decrease in the population of the orthogonal conformer.