Benzyl Phenyl Ether Research Articles

Three-dimensional structures of substituted benzylphenyl ethers

Forty nine three-dimensional crystal structures of a benzylphenyl ether fragment retrieved from the Cambridge Structural Database were confronted with computed conformational maps of the fragment. Due to the symmetry the number of analyzed fragments rose to 98. When an endocyclic torsion angle of a phenyl ring deviates from 0° the adjacent torsion angle is deformed in opposite direction compensating thus the deviation from planarity. The shape of the fragment is mainly controlled by torsion angles τ1 = C-C-O-CH2, τ2 = C-O-CH2-C, and τ3 = O-CH2-C-C. The attachment of both phenyl rings to the -CH2-O- moiety is not symmetrical and the deformation depends on the value of the τ3 angle. In the crystal, the fragment prefers conformation with τ1 around 0°, τ2 around 180° and with broad bimodal distribution of τ3 around 0° and ±90° despite the fact that energetically equivalent regions exist in the potential energy maps for τ2 values near 60° and 300° and that many crystal structures with τ3 around 0° lie in higher energetical regions than those with τ3 around 90°. Thus a significant difference between the crystal and simulated gas phase conformations was observed supporting the hypothesis that crystals prefer flatter and more storable molecular conformations.

The Benzylphenylether thermolysis mechanism: Insights from phase behavior

AbstractThe thermolysis of benzylphenylether (BPE) was examined at 320°C in liquid, vapor, and supercritical methanol phases as a probe of the reaction mechanism. Toluene and phenol were the major products in all cases, but observed selectivities were dependent upon the reaction phase. Isotopic labeling experiments demonstrated that methanol participated in the reaction network as a hydrogen donor through a free‐radical mechanism. These results are consistent with free‐radical steps for neat BPE primary pyrolysis that include BPE fission followed by hydrogen abstraction and radical recombination reactions. A detailed set of 21 free‐radical steps quantitatively explains the dependence of the selectivity and conversion on the phase behavior.

Effect of temperature and hydrogen partial pressure on the hydrogenolysis reaction of model compounds

The hydrogenolysis reaction of dibenzyl and benzyl phenyl ether has been studied varying temperature and hydrogen partial pressure. The increase in hydrogen partial pressure suppressed the formation of condensation products and accelerated the hydrogenation of aromatic ring, dehydroxylation and splitting the central CC or CO bonds. The increase in temperature firstly caused the saturation of aromatic ring and splitting of central bonds, then accelerated dehydroxylation. At higher temperatures the hydrogenation of aromatic rings was suppressed.

Substituent dependence of the .pi.-acceptor-induced bond cleavage reactions of benzyl phenyl ethers

The relative C-O bond cleavage reaction rates (k{sub rel}) of eight substituted benzyl phenyl ethers (BPE's) have been measured. These C-O bond cleavage reactions were thermally initiated by 2,3-dichloro-5,6-dicyanoquinone (DDQ). The equilibrium constants (K) for charge-transfer complex formation of these BPE's with the electron acceptors DDQ and TCNE in the solvent methylene chloride have also been determined at room temperature. The best correlation of log k{sub rel} for DDQ reactions has been observed with the {sigma}{sup +} substittuent parameter. A primary kinetic isotope effect has been observed in these reactions. From this data, hydride transfer to dDQ is the rate-determining step of the reaction.

The synthesis of substituted benzyl phenyl ethers: An undergraduate organic chemistry experiment

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTThe synthesis of substituted benzyl phenyl ethers: An undergraduate organic chemistry experimentKimberly Dilts and Marc Durand Cite this: J. Chem. Educ. 1990, 67, 1, 74Publication Date (Print):January 1, 1990Publication History Received3 August 2009Published online1 January 1990Published inissue 1 January 1990https://doi.org/10.1021/ed067p74RIGHTS & PERMISSIONSArticle Views1664Altmetric-Citations7LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (603 KB) Get e-Alerts Get e-Alerts

Benzyl Ethers as Chromophores in the Exciton Chirality Method for Absolute Configurational Studies of Compounds with Hindered Hydroxyls

Abstractp‐Phenylbenzyl ethers and, in general, other benzyl ethers, can be substituted for benzoates in the exciton chirality method for determining absolute configurations of polyols. This is useful when dealing with hydroxyl groups that resist acylation. If necessary, the phenylbenzylates can be oxidized to the corresponding phenylbenzoates with concomitant enhancement in sensitivity.

One electron oxidations of benzyl and 2-phenylethyl phenyl ethers. The fate of the intermediate radical cations

The one electron oxidations of benzyl phenyl ether ( 1 ), 2-phenylethyl phenyl ether ( 2 ) and 2-(4-methoxyphenyl)ethyl phenyl ether ( 3 ) promoted (a) by cerium(IV) ammonium nitrate (CAN) in AcOH, (b) electrochemically in AcOH-MeCN/AcOK and (c) photochemically in MeCN, in the presence of 9,10-dicyanoanthracene (DCA), have been investigated. With 1 benzaldehyde forms, under all the reaction conditions, accompanied by products of acetoxylation at the phenoxy ring (conditions a and b) or by phenyl benzoate (condition c). The CAN-promoted and the electrochemical oxidation of 2 exclusively lead to substitution at the phenoxy ring, whereas only-side-chain attack at the benzylic carbon occurs in all of the reactions of 3 , with formation of 4-methoxybenzaldehyde and products of side-chain oxidation. Phenyl 4-methoxybenzoate is also formed (conditions b and c). However, when the electrochemical oxidation is carried out in the absence of AcOK, only a product of intramolecular ring closure forms. These results allow one to draw some interesting conclusion on the competition between the various reaction pathways available to the cation radicals which are the first formed reaction intermediates in these one electron processes.

Hydrogen transfer in the hydrogenation of model compounds

Dibenzyl and benzyl phenyl ether were reacted together in naphthalene, tetralin and decalin, respectively under hydrogen or nitrogen atmosphere. Stabilized nickel was used as catalyst, and reaction was carried out at 250 °C and at 400 °C. The main reaction was the direct hydrogenation of samples by gaseous hydrogen on the catalyst surface.

Partial Characterization of an Enzyme from the Fungus Ascochyta rabiei for the Reductive Cleavage of Pterocarpan Phytoalexins to 2′-Hydroxyisoflavans

Crude protein extracts from the chickpea (Cicer arietinum L.) pathogenic fungus Ascochyta rabiei catalyze the NADPH dependent conversion of the pterocarpan phytoalexins medicarpin and maackiain to 1) 2′-hydroxyisoflavans, 2) 1 a-hydroxypterocarp-1,4-diene-3-one, and 3) 10,2′-dihydroxyisoflav-8-ene-7-one derivatives. A pterocarpan : NADPH oxidoreductase which cleaves the benzylphenyl ether bond of the phytoalexins was purified some 100-fold and partially characterized with regard to its kinetic properties. The oxidoreductase was shown to be specific for NADPH and 3-hydroxypterocarpans. The enzyme appears to be constitutively expressed by A. rabiei.

ChemInform Abstract: Electron Apportionment in Cleavage of Radical Anions. Part 1. Nitro‐Substituted Benzyl Phenyl Ethers.

AbstractCleavage of the radical anions (Ia) yields the toluene (IV) as the only detected product from low concentrated solutions.

Reaction of benzyl phenyl ether over various molten metal catalysts

Benzyl phenyl ether, as a model for ether linkages in coal structures, was reacted at temperatures ranging from 400 °C to 500 °C over eight molten metal catalysts (In, Ga, Tl, Cd, Zn, Sn, Pb, Bi). Phenol, bibenzyl, toluene, benzene, ethylbenzene, and propylbenzene were formed together with o-benzylphenol. The conversions to the first six compounds showed little catalyst dependence but showed characteristic mutual correlations. A reaction scheme capable of explaining these experimental results was proposed. The extent of conversion to o-benzylphenol varied with the catalyst, exhibiting a ‘volcano-shaped’ correlation with the heat of fusion of the catalyst metal. Formation of catalytic ensembles comprising surface catalyst atoms and a transition state molecule was considered to be responsible for the volcano-shaped correlation.

Electron apportionment in cleavage of radical anions. 1. Nitro-substituted benzyl phenyl ethers

Electron apportionment in cleavage of radical anions. 1. Nitro-substituted benzyl phenyl ethers

ChemInform Abstract: Aromatic Rearrangements in the Benzene Series. Part 4. Intramolecularity of Both the ortho‐ and para‐Rearrangements of Benzyl Phenyl Ether as Shown by Labelling Experiments (Nachweis auch des p‐Isomers im Gegensatz zu früheren Ergebnissen, o: p = 4.7.

Chemischer InformationsdienstVolume 17, Issue 2 Preparative Organic Chemistry ChemInform Abstract: Aromatic Rearrangements in the Benzene Series. Part 4. Intramolecularity of Both the ortho- and para-Rearrangements of Benzyl Phenyl Ether as Shown by Labelling Experiments (Nachweis auch des p-Isomers im Gegensatz zu früheren Ergebnissen, o: p = 4.7. L. S. HART, L. S. HARTSearch for more papers by this authorC. R. WADDINGTON, C. R. WADDINGTONSearch for more papers by this author L. S. HART, L. S. HARTSearch for more papers by this authorC. R. WADDINGTON, C. R. WADDINGTONSearch for more papers by this author First published: January 14, 1986 https://doi.org/10.1002/chin.198602105AboutPDF 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 onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume17, Issue2January 14, 1986 RelatedInformation

π-Acceptor induced thermal reactions: Bond cleavage reactions

TCNQ, TCNQF4, and DDQ have been found to initiate unusual bond breakage reactions. Benzylphenyl sulfide ( BPS) and benzylphenyl ether ( BPE) undergo cleavage of their interaryl bonds while bibenzyl ( BB) does not cleave the interaryl bond and forms only trans-stilbene ( TS) when reacted under the same conditions.

Catalytic activities of binary metal oxides containing iron for hydrocracking of benzyl phenyl ether and diphenyl ether

Hydrocracking of benzyl phenyl ether and diphenyl ether has been carried out over a series of iron catalysts (Fe 2O 3, Fe 2O 3Al 2O 3, Fe 2O 3ZnO, Fe 2O 3ZrO 2, Fe 2O 3MgO and Fe 2O 3SiO 2) and reference catalysts ( CoOMoO 3 Al 2O 3 , NiOMoO 3 Al 2O 3 and SiO _Al 2O 3) to search for active and selective catalysts, and to elucidate the catalyst properties of relevance for CO bond cleavage. Among the iron catalysts, Fe 2O 3ZnO, Fe 2O 3ZrO 2 and Fe 2O 3MgO exhibited relatively high activities and selectivities. The important property of catalysts relevant to hydrocracking of the ethers is the ability to accomplish hydrogenation. Acidic properties of the catalysts cause condensation and rearrangement of the reactants. The features of the iron catalysts are compared with those of molybdenum catalysts, and the reaction mechanisms discussed.

Kinetics of Phase Transfer Catalytic Preparation of Benzyl Phenyl Ether

AbstractBenzyl phenyl ether is prepared in a well‐stirred batch reactor from phenol and benzyl chloride using tetrabutylammonium iodide as phase transfer catalyst. Phenol with sodium hydroxide is dissolved in water as the aqueous phase, and benzyl chloride is dissolved in toluene as the organic phase. Tetrabutylammonium iodide gives high reaction rate without the formation of micelles during the reaction. The reaction mechanism is verified by infrared spectrum study and other experimental observations. The kinetics of the reaction of benzyl chloride is modelled as a first‐order chemical reaction. The cocatalytic effect of the iodide ion, and salting out effect on the overall reaction rate are discussed in detail using experimental data.

Influence of substituents on the chemical shifts of fluorine in 2- and 3-Fluorosubstituted phenyl benzyl ethers

1. The19F-{1H} NMR spectra of a series of substituted 3- and 2-fluorophenyl benzyl ethers were investigated. 2. With respect to the effectiveness of the transmission of electronic influences of the substituents in the benzene group on the indicator fluorine atom in fluorophenyl benzyl ethers, the 3-fluorophenyl group is less informative than the 4-fluorophenyl group, while the 2-fluorophenyl; group gives no information.

Effects of molten tin surface upon the reaction of benzyl phenyl ether

Molten tin catalyst enhanced the degree of isomerization of benzyl phenyl ether to o-benzylphenol at 430–500 °C. This suggests that the catalyst surface has provided the primary radical pair with a dual site, which promotes reaction between them.

Thermal decomposition of benzyl phenyl ether and benzyl phenyl ketone in the presence of tetralin

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTThermal decomposition of benzyl phenyl ether and benzyl phenyl ketone in the presence of tetralinYoshiki Sato and Toshio YamakawaCite this: Ind. Eng. Chem. Fundamen. 1985, 24, 1, 12–15Publication Date (Print):February 1, 1985Publication History Published online1 May 2002Published inissue 1 February 1985https://doi.org/10.1021/i100017a003RIGHTS & PERMISSIONSArticle Views309Altmetric-Citations13LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (428 KB) Get e-Alerts

Gas phase generation and reactions of o-dialkylaminobenzyl and o-dialkylaminophenoxyl radicals

Generation of the title radicals was effected by flash vacuum pyrolysis of benzyl phenyl ethers, and O-allyl ethers, respectively. The major products are formed by a multi-step sequence involving (i) intramolecular hydrogen transfer from the alkylamino group to the initial radical centre, (ii) rearrangement of the resulting aminoalkyl radical, and (iii) expulsion of the nitrogen residue to give a benzyl radical which leads to products.