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Journal articles on the topic 'Ether(alkyl allyl)|ent'

Author: Grafiati

Published: 4 June 2021

Last updated: 5 February 2022

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1

Dutta, Lakshmi Narayan, Banani De, Godhuli Pal, and Amarendra Patra. "Feasibility of sigmatropic rearrangement on electron-deficient coumarinyl ketones." Canadian Journal of Chemistry 86, no. 5 (May 1, 2008): 401–9. http://dx.doi.org/10.1139/v08-037.

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Different alkyl/aryl 7-hydroxy-8-coumarinyl ketones were converted to 7-O-allyl and 7-O-cyclohexenyl ethers and the study of hitherto unreported sigmatropic rearrangement on 7-O-allyl and 7-O-cyclohex-2'-ene-1'-ylcoumarinyl ketones prepared is accounted herein. The rearrangement yielded alkyl/aryl 6-allyl-7-hydroxy-8-coumarinyl ketones 3 and alkyl/aryl 6-cyclohex-2'-en-1'-yl-7-hydroxy-8-coumarinyl ketones 7 as the major products. Interestingly, unusual selectivity was observed in the case of alkyl 7-O-allylcoumarinyl ketones. Thus alkyl 3-allyl-7-hydroxy-8-coumarinyl ketones 4 and alkyl 8-allyl-7-hydroxy-6-coumarinyl ketones 5 were the outcome from alkyl 7-O-allyl-8-coumarinyl ketones and alkyl 4-methyl-7-O-allyl-8-coumarinyl ketones, respectively, albeit in minor yields.Key words: allyloxycoumarinyl ketones, 7-O-cyclohex-2'-en-1'-ylcoumarinyl ketones, sigmatropic rearrangement, 3-allylcoumarinyl ketones, 8-allylcoumarinyl ketones.

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2

Toncheva-Moncheva, Natalia, Miroslav Dangalov, Nikolay G. Vassilev, and Christo P. Novakov. "Thiol–ene coupling reaction achievement and monitoring by “in situ” UV irradiation NMR spectroscopy." RSC Advances 10, no. 42 (2020): 25214–22. http://dx.doi.org/10.1039/d0ra03902k.

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3

Grossi, Vincent, Damien Mollex, Arnauld Vinçon-Laugier, Florence Hakil, Muriel Pacton, and Cristiana Cravo-Laureau. "Mono- and Dialkyl Glycerol Ether Lipids in Anaerobic Bacteria: Biosynthetic Insights from the Mesophilic Sulfate Reducer Desulfatibacillum alkenivorans PF2803T." Applied and Environmental Microbiology 81, no. 9 (February 27, 2015): 3157–68. http://dx.doi.org/10.1128/aem.03794-14.

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ABSTRACTBacterial glycerol ether lipids (alkylglycerols) have received increasing attention during the last decades, notably due to their potential role in cell resistance or adaptation to adverse environmental conditions. Major uncertainties remain, however, regarding the origin, biosynthesis, and modes of formation of these uncommon bacterial lipids. We report here the preponderance of monoalkyl- and dialkylglycerols (1-O-alkyl-, 2-O-alkyl-, and 1,2-O-dialkylglycerols) among the hydrolyzed lipids of the marine mesophilic sulfate-reducing proteobacteriumDesulfatibacillum alkenivoransPF2803Tgrown onn-alkenes (pentadec-1-ene or hexadec-1-ene) as the sole carbon and energy source. Alkylglycerols account for one-third to two-thirds of the total cellular lipids (alkylglycerols plus acylglycerols), depending on the growth substrate, with dialkylglycerols contributing to one-fifth to two-fifths of the total ether lipids. The carbon chain distribution of the lipids ofD. alkenivoransalso depends on that of the substrate, but the chain length and methyl-branching patterns of fatty acids and monoalkyl- and dialkylglycerols are systematically congruent, supporting the idea of a biosynthetic link between the three classes of compounds. Vinyl ethers (1-alken-1′-yl-glycerols, known as plasmalogens) are not detected among the lipids of strain PF2803T. Cultures grown on different (per)deuteratedn-alkene,n-alkanol, andn-fatty acid substrates further demonstrate that saturated alkylglycerols are not formed via the reduction of hypothetic alken-1′-yl intermediates. Our results support an unprecedented biosynthetic pathway to monoalkyl/monoacyl- and dialkylglycerols in anaerobic bacteria and suggest thatn-alkyl compounds present in the environment can serve as the substrates for supplying the building blocks of ether phospholipids of heterotrophic bacteria.

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4

Liepa, AJ, AJ Liepa, JS Wilkie, JS Wilkie, KN Winzenberg, and KN Winzenberg. "Preparation of Some 1-Alkyl-4-[1-(ethoxyimino)butyl]-3-hydroxy-5-oxocyclohex-3-ene-1-carboxylic Acid Ester and Amide Herbicides by Reductive Alkylation of 3,5-Dimethoxybenzoic Acid." Australian Journal of Chemistry 42, no. 8 (1989): 1217. http://dx.doi.org/10.1071/ch9891217.

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Reductive alkylation of 3,5-dimethoxybenzoic acid with haloalkanes afforded the 1-alkyl- 3,5-dimethoxycyclohexa-2,5-diene-1-carboxylic acid derivatives (3a-e) which, upon esterification and hydrolysis, furnished methyl 1-alkyl-3-hydroxy-5-oxocyclohex-3-ene-l-carboxylate derivatives (4f-j). Reaction of (4f-j) with butyric anhydride gave methyl 1-alkyl-4-butyryl- 3-hydroxy-5-oxocyclohex-3-ene-1-carboxylate derivatives (6a-e) which were converted into methyl 1-alkyl-4-[1-( ethoxyimino )butyl]-3-hydroxy-5-oxocyclohex-3-ene-1-carbo xyate derivatives (2a-e). Similarly, the oxime O-ether derivative (2f) was prepared from the amide (41), obtained from reaction of (3b) with N,N′- carbonyldiimidazole and dimethylamine followed by hydrolysis.

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5

Wright, Andrew D., and Richard D. Bowen. "Investigation of the mechanism of alkyl radical elimination from ionised pentenyl methyl and hexenyl methyl ethers by analysis of the collision-induced dissociation mass spectra of C4H7O+ and C5H9O+ ions." Canadian Journal of Chemistry 71, no. 7 (July 1, 1993): 1073–85. http://dx.doi.org/10.1139/v93-143.

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Collision-induced dissociation (CID) mass spectra are reported for C4H7O+ and C5H9O+ ions generated by loss of an alkyl radical from 11 isomers of C5H9OCH3+• and 8 isomers of C6H11OCH3+• produced by ionisation of alkenyl methyl ethers derived from stable alkenols. The oxonium product ions have acyclic structures (CH=CHCH=O+CH3 for C4H7O+; CH2=CH(CH3)C=O+CH3, CH3CH=CHCH=O+CH3, or CH2=(CH3)CCH=O+CH3 in the case of C5H9O+). Elimination of a methyl radical does not always occur by simple α-cleavage. Expulsion of an alkyl substituent attached to a carbon atom at either end of the C=C double bond also takes place readily; this process sometimes competes with or pre-empts α-cleavage, as is shown by 2H-labelling experiments. Plausible mechanisms for this σ′-cleavage are considered. A route involving a 1,2-H shift to the radical centre of a distonic ion, followed by γ-cleavage of the resultant ionised enol ether, is shown to provide the most accurate unifying description of this unusual fragmentation. The mechanistic significance of this interpretation of the σ′-cleavage is discussed by analysing the reverse reaction (addition of an alkyl radical to a methyl cationated enal) in frontier molecular orbital terms. A comparison is made between the mechanisms by which an alkyl radical is lost from ionised alkenyl methyl ethers by σ′-cleavage and the parallel process starting from ionised carboxylic acids or isomeric distonic ions derived from these CnH2n+1CO2H+• species. Both classes of fragmentation are best understood to occur via γ-cleavage of a distonic ion of general structure R1CH2CH•C+(X)OR2 (R1 = alkyl; X = OH, R2 = H; or X = H, R2 = CH3), thus yielding (R′)• and CH2 = CHC+(X)OR2.

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6

Nilsson, Camilla, Neil Simpson, Michael Malkoch, Mats Johansson, and Eva Malmström. "Synthesis and thiol-ene photopolymerization of allyl-ether functionalized dendrimers." Journal of Polymer Science Part A: Polymer Chemistry 46, no. 4 (December 28, 2007): 1339–48. http://dx.doi.org/10.1002/pola.22474.

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7

Yu, Ga-Er, Frank Heatley, Colin Booth, and Trevor G. Blease. "Anionic polymerization of propylene oxide: Isomerization of allyl ether to propenyl ether end groups." Journal of Polymer Science Part A: Polymer Chemistry 32, no. 6 (April 30, 1994): 1131–35. http://dx.doi.org/10.1002/pola.1994.080320615.

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8

Yu, Qing Bo, Xian Hua Li, Yu Lun Tao, and Guo Jun Cheng. "The Characteristic Research of Two Kinds of Block Polymer." Advanced Materials Research 356-360 (October 2011): 74–77. http://dx.doi.org/10.4028/www.scientific.net/amr.356-360.74.

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Dual end and single end MacroRAFT agents of polystyrene were obtained respectively by polymerizations of styrene in the presence of benzyl 1H-imidazole-1- carbodithioate (BICDT) and 4,4‘-bis(imidazole-1-carbodithioatemethyl)biphenyl (ICTMP) via the thermal initiation. Then copolymerization of allyl glycidyl ether（AGE） with methyl acrylate（MA） was performed to prepare the functional block copolymers in the presence of PSt maeorRATF agents. The results show that the process has good characteristics of living free radical polymerization. However, the top monomer conversion of triblock copolymers comparing diblock copolymers is lower under the same theory molecular weight and the content of monomer.

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9

Niemczyk, Edyta M., Alvaro Gomez-Lopez, Jean R. N. Haler, Gilles Frache, Haritz Sardon, and Robert Quintana. "Insights on the Atmospheric-Pressure Plasma-Induced Free-Radical Polymerization of Allyl Ether Cyclic Carbonate Liquid Layers." Polymers 13, no. 17 (August 25, 2021): 2856. http://dx.doi.org/10.3390/polym13172856.

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Plasma-induced free-radical polymerizations rely on the formation of radical species to initiate polymerization, leading to some extent of monomer fragmentation. In this work, the plasma-induced polymerization of an allyl ether-substituted six-membered cyclic carbonate (A6CC) is demonstrated and emphasizes the retention of the cyclic carbonate moieties. Taking advantage of the low polymerization tendency of allyl monomers, the characterization of the oligomeric species is studied to obtain insights into the effect of plasma exposure on inducing free-radical polymerization. In less than 5 min of plasma exposure, a monomer conversion close to 90% is obtained. The molecular analysis of the oligomers by gel permeation chromatography coupled with high-resolution mass spectrometry (GPC-HRMS) further confirms the high preservation of the cyclic structure and, based on the detected end groups, points to hydrogen abstraction as the main contributor to the initiation and termination of polymer chain growth. These results demonstrate that the elaboration of surfaces functionalized with cyclic carbonates could be readily elaborated by atmospheric-pressure plasmas, for instance, by copolymerization.

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10

Liu, Michael T. H., Yuri N. Romashin, and T. K. Venkatachalam. "Photolysis of 3-chloro-3-aryldiazirines in the presence of amines and allyl alcohol." Canadian Journal of Chemistry 72, no. 9 (September 1, 1994): 1961–65. http://dx.doi.org/10.1139/v94-250.

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When photolysis of arylchlorodiazirines is performed in the presence of either alkyl- or allyl-substituted amines, either N-alkyl- or N-allyl-substituted amines result as the sole high-yield (64-93%) products. Photolysis in the presence of phenylallylamine produces a rearranged product in poor yield (11–15%) whereas the reaction of allyl alcohol with arylchlorocarbene gives exclusively diallyl acetals in high yield (70%). The rate constants for these reactions were obtained by laser flash photolysis. Allyl phenyl ether forms a cyclopropanated product when treated with arylchlorocarbene. The different behaviour of these compounds may be attributed to the nucleophilicity at the nitrogen and oxygen centres of these compounds, when the latter are subjected to the substitutions described above. The formation of a cyclopropanated product when allyl phenyl ether is used differs from the reaction of bis (methoxycarbonyl) carbene with allyl ethers, as reported in the literature. The formation of this cyclopropanated product demonstrates the absence of an oxonium ylide intermediate during the reaction.

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11

Tanino, Keiji, Hisashi Shoda, Takashi Nakamura, and Isao Kuwajima. "Ene reaction of 2-(alkylthio)allyl silyl ether involving a chirality transfer." Tetrahedron Letters 33, no. 10 (March 1992): 1337–40. http://dx.doi.org/10.1016/s0040-4039(00)91616-2.

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12

Arnold, Donald R., Mary S. W. Chan, and Kimberly A. McManus. "Photochemical nucleophile–olefin combination, aromatic substitution (photo-NOCAS) reaction, Part 12. Factors controlling the regiochemistry of the reaction with alcohol as the nucleophile." Canadian Journal of Chemistry 74, no. 11 (November 1, 1996): 2143–66. http://dx.doi.org/10.1139/v96-243.

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The photo-NOCAS reaction that combines methanol, serving as the nucleophile, and the radical cation of 4-methyl-1,3-pentadiene (14+•), substituting on the 1,4-dicyanobenzene radical anion (1−•), yields (E)-1-(4-cyanophenyl)-4-methoxy-4-methyl-2-pentene (15) as the major product. This regioisomer arises from bonding of methanol to C-4, the more heavily alkyl-substituted carbon of the diene, giving the less alkyl-substituted allylic radical. All previous examples of the photo-NOCAS reaction have yielded major adduct(s) having regiochemistry consistent with the anti-Markovnikov rule; the more heavily substituted (more stable?) β-alkoxyalkyl radical was the predominant intermediate. Empirically derived heats of formation and high-level ab initio molecular orbital calculations (MP2/6-31G*//HF/6-31G*) provide convincing evidence that of the two alternative allylic radicals, generated upon addition of methanol to 14+•, that which has the more alkyl substituted allylic radical moiety is, in fact, not the more stable. Of course, the total structure of the intermediate must be considered; the stabilizing effect of alkyl substitution on the carbon next to the oxygen of the ether moiety cannot be ignored. Ab initio molecular orbital calculations (MP2/6-31G*//HF/6-31G*) are reported for the radical cations of 2-methylpropene (2+•), 2-methyl-2-butene (6+•), 2-methyl-1,3-butadiene (9+•), 4-methyl-1,3-pentadiene (14+•), and 2,4-dimethyl-1,3-pentadiene (18+•) Calculations were also carried out on possible intermediates (bridged radical cations, distonic radical cations, and β-alkoxyalkyl radicals) involved upon reaction of these radical cations with methanol. Results of these calculations provide a basis for explaining/predicting the regiochemistry of the photo-NOCAS reaction involving methanol as the nucleophile: the major adduct(s) result(s) from attachment of methanol to that end of the alkene or diene which gives rise to the more stable intermediate radical. The more stable radical is not necessarily the more heavily alkyl substituted. Key words: photoinduced electron transfer, radicals, radical cations, ab initio molecular orbital calculations.

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13

Nasser, Boubker, Claude Morpain, Bernard Laude, and Norbert Latruffe. "Synthesis and characterization of chemical intermediates of acyl or alkyl phospholipids." Canadian Journal of Chemistry 70, no. 8 (August 1, 1992): 2319–24. http://dx.doi.org/10.1139/v92-293.

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Precursors of phospholipids or ether lipids were synthesized from D-mannitol, i.e., 1-O-myristoyl-2-O-benzyl-sn-glycerol 11 and 1-O-hexadecyl-2-O-benzyl-sn-glycerol 13. The chemical pathways involved sequential protection reactions using allyl, triphenylmethyl, or benzyl groups via 3-O-allyl-sn-glycerol. Eleven intermediates were isolated and for the first time characterized with their spectrometric (especially 1H nmr) and physical parameters and yield. This work allowed preparation of chemically defined membrane phospholipids from compound 11 as well as ether lipids from compound 13 with cell mediator activities bearing different probes such as photoactivatable, fluorescent, or radioactive groups.

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14

Tasic, Srba, Branislav Bozic, and Branko Dunjic. "Hyperbranched urethane-acrylates." Chemical Industry 58, no. 11 (2004): 505–13. http://dx.doi.org/10.2298/hemind0411505t.

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The synthesis, characterization and UV-curing of hyperbranched urethaneacrylates (HB-UA) were investigated in this study. They were evaluated as oli-gomers in model UV curable coatings. HB-UAs were synthesized by reaction of an aliphatic hyperbranched polyester of the second generation (HBRG2) and an isocyanate adduct, obtained by the reaction of isophoronediisocyana-te and different hydroxy alkyl acrylates. Their thermal properties and viscosities depend on the degree of modification of HBRG2 and the type of hydroxy alkyl acrylate used. The introduction of a flexible alkoxylated spacer between the HBP core and acrylate end groups reduces steric hindrance by moving the cross linkable acrylate groups away from the HBP core and increase its reactivity. Due to the presence of abstractable H-atoms in the ?-position to the ether links, HB-UAs based on poly(ethylene oxide) monoacrylate are very reactive and do not show oxygen inhibition. The obtained coatings combine a high cross linking density with flexible segments between the cross links, which results in a good compromise between hardness and flexibility and have the potential to be used in different UV-curing applications.

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15

Ollevier, Thierry, and Topwe M. Mwene-Mbeja. "Diastereoselective bismuth triflate catalyzed Claisen rearrangement of 2-alkoxycarbonyl-substituted allyl vinyl ethers." Canadian Journal of Chemistry 86, no. 3 (March 1, 2008): 209–12. http://dx.doi.org/10.1139/v07-149.

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In the presence of a catalytic amount of bismuth triflate, 2-alkoxycarbonyl-substituted allyl vinyl ethers as a mixture of enol ether double bond isomers were smoothly converted into the β,γ-alkyl-substituted α-keto esters. The isomerization reaction proceeded rapidly to afford smoothly the α-keto esters in good to excellent yields using catalytic amounts of Bi(OTf)3·4H2O (1 mol%). (Z,Z)-2-iso-Propyloxycarbonyl-substituted allyl vinyl ethers 3Z,Z afforded the corresponding β,γ-alkyl-substituted α-keto esters 4 with very good syn diastereoselectivity.Key words: bismuth; bismuth(III) triflate; Claisen rearrangement; allyl vinyl ethers.

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16

Tohyama, Yoshitomo, Keiji Tanino, and Isao Kuwajima. "Highly Stereoselective Ene Reaction of Aldimines with 2-(Alkylthio)allyl Silyl Ethers." Journal of Organic Chemistry 59, no. 3 (February 1994): 518–19. http://dx.doi.org/10.1021/jo00082a004.

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17

Nakamura, Takashi, Keiji Tanino, and Isao Kuwajima. "Highly stereoselective chelation controlled ene-reaction of 2-(alkylthio)allyl silyl ethers." Tetrahedron Letters 34, no. 3 (January 1993): 477–80. http://dx.doi.org/10.1016/0040-4039(93)85106-7.

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18

Elmer, Stephanie L., and Steven C. Zimmerman. "Cross-Linking Dendrimers with Allyl Ether End-Groups Using the Ring-Closing Metathesis Reaction." Journal of Organic Chemistry 69, no. 21 (October 2004): 7363–66. http://dx.doi.org/10.1021/jo049368v.

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19

TANINO, K., H. SHODA, T. NAKAMURA, and I. KUWAJIMA. "ChemInform Abstract: Ene Reaction of 2-(Alkylthio)allyl Silyl Ether Involving a Chirality Transfer." ChemInform 23, no. 40 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199240080.

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20

Vikkula, Anne, and Tapani Vuorinen. "The formation of aromatic end group structures in O-alkyl substituted celluloses under alkaline pulping conditions." Holzforschung 60, no. 4 (July 1, 2006): 378–82. http://dx.doi.org/10.1515/hf.2006.059.

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Abstract UV resonance Raman (UVRR) spectroscopy was used to study changes in the structure of reducing end groups of O-alkyl substituted celluloses under conditions simulating the initial phase of soda pulping. The derivatives studied were carboxymethyl cellulose (CMC) with a degree of substitution (DS) of 0.58 and methyl cellulose (MC) with DS of 1.64–1.95. Hot alkaline treatments were carried out in solutions of sodium hydroxide (0.1–1 M) at 95°C in the presence of creosol as a lignin model compound. Alkali-stable aromatic end groups were generated in both cellulose ethers. Moreover, the end groups of methyl cellulose were extensively condensed with creosol. The results demonstrate that aromatisation and condensation depend on the pH and reaction time.

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21

Tanino, Keiji, Takashi Nakamura, and Isan Kuwajima. "Highly threo-selective ene-reaction of 2-(alkylthio)allyl silyl ethers with aldehydes." Tetrahedron Letters 31, no. 15 (January 1990): 2165–68. http://dx.doi.org/10.1016/0040-4039(90)80099-8.

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22

Trey, Stacy M., Camilla Nilsson, Eva Malmström, and Mats Johansson. "Thiol–ene networks and reactive surfaces via photoinduced polymerization of allyl ether functional hyperbranched polymers." Progress in Organic Coatings 67, no. 3 (March 2010): 348–55. http://dx.doi.org/10.1016/j.porgcoat.2009.10.023.

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23

Trey, Stacy M., Camilla Nilsson, Eva Malmström, and Mats Johansson. "Thiol–ene networks and reactive surfaces via photoinduced polymerization of allyl ether functional hyperbranched polymers." Progress in Organic Coatings 68, no. 1-2 (May 2010): 151–58. http://dx.doi.org/10.1016/j.porgcoat.2010.03.001.

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24

Knicker, Heike, Marta Velasco-Molina, and Michael Knicker. "2D Solid-State HETCOR 1H-13C NMR Experiments with Variable Cross Polarization Times as a Tool for a Better Understanding of the Chemistry of Cellulose-Based Pyrochars—A Tutorial." Applied Sciences 11, no. 18 (September 15, 2021): 8569. http://dx.doi.org/10.3390/app11188569.

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The chemistry and nature of biochars are still far from being well understood. In the present work, solid-state 2D HETCOR 1H-13C NMR spectroscopy is introduced for an improved characterization of the aromatic network in biochars. To that end, a pyrochar obtained from the pyrolysis of cellulose at 350 °C for 1 h was used as an example. Variation of the contact time during cross polarization from 50 µs, to 200 µs and 1000 µs gave information about the protonation degree of the different C groups and their interactions. We demonstrated that carbohydrates did not survive the used pyrolysis conditions. Therefore, O-alkyl C was assigned to ethers. Phenols were not identified to a higher extent suggesting that furan and benzofuran-type units determine the O-functionality of the aromatic domains. The latter are directly connected to alkyl chains. Those features are expected to affect chemical but also physical properties of the biochar. Based on our results, we developed a new concept describing the nature of the aromatic network in the studied cellulose-based pyrochars. The latter contrasts common views about the chemical nature of biochar, possibly because pyrolysis temperatures > 350 °C are required for achieving advanced condensation of the aromatic domains.

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25

Parzuchowski, Paweł G., Aleksandra Świderska, Marlena Roguszewska, Karolina Rolińska, Dominik Wołosz, and Mariusz Mamiński. "Hyperbranched Poly(ether-siloxane)s Containing Ammonium Groups: Synthesis, Characterization and Catalytic Activity." Polymers 12, no. 4 (April 7, 2020): 856. http://dx.doi.org/10.3390/polym12040856.

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In this article we report an easy synthetic route towards hyperbranched polyglycerols (Amm-HBPGs) containing trimethylammonium groups and siloxane or hydroxyl end-groups. Siloxane derivatives of Amm-HBPGs were synthesized in an efficient five-step procedure including an anionic ring opening copolymerization of the phthalimide-epoxy monomer with glycidol, followed by reactions with allyl bromide, hydrosililation with hydrogenheptamethyltrisiloxane, hydrazinolysis of phthalimide groups and quaternization of resulting amine groups with methyl iodide. Hydroxyl derivatives were obtained by quaternization of previously reported aminated HBPG’s with methyl iodide. Polymeric products were characterized using various NMR techniques, FTIR, and elemental analysis. Both Amm-HBPGs were shown to be effective in catalysis of addition of CO2 to oxirane. The hydrophilic catalysts showed higher efficiency but synthesis of ethylene carbonate was accompanied by formation of small amounts of ethylene glycol. The siloxane-containing catalyst was easily separable from reaction mixture showing high potential in the process of converting carbon dioxide into valuable chemical raw materials.

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26

Schmidt, H., and E. Heinz. "Direct desaturation of intact galactolipids by a desaturase solubilized from spinach (Spinacia oleracea) chloroplast envelopes." Biochemical Journal 289, no. 3 (February 1, 1993): 777–82. http://dx.doi.org/10.1042/bj2890777.

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In plants, polyenoic fatty acids are synthesized by desaturase enzymes which use acyl groups of membrane lipids as substrates. To provide direct ‘in vitro’ evidence for this reaction, we solubilized envelope membranes from spinach (Spinacia oleracea) chloroplasts with Triton X-100 to release a membrane-bound n-6 desaturase. In the presence of oxygen and reduced ferredoxin, the solubilized enzyme desaturated a variety of substrates, such as free oleic acid, free erucic acid, 1-oleoyl-sn-glycerol 3-phosphate and the three galactolipids 1-oleoyl-2-(7′-cis-hexadecenoyl)-3-beta-D-galactopyranosyl-sn-glycerol, 1,2-dioleoyl-3-beta-D-galactopyranosyl-sn-glycerol and the ether analogue 1,2-di-(9′-cis-octadecenyl)-3-beta-D-galactopyranosyl-sn- glycerol. The in vitro desaturation of these exogenously added complex lipids with ester- and ether-linked substrate chains is unambiguous evidence for lipid-linked desaturation. The enzyme measures the insertion of the new double bond from the methyl end and the existing (n-9)-cis-double bond of an appropriate acyl or alkyl chain. The distal part of the substrate group, normally the carboxy end of a fatty acyl residue, is of less importance and, in particular, its activation in thioester form is not required.

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27

TOHYAMA, Y., K. TANINO, and I. KUWAJIMA. "ChemInform Abstract: Highly Stereoselective Ene Reaction of Aldimines with 2-(Alkylthio) allyl Silyl Ethers." ChemInform 25, no. 26 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199426048.

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28

NAKAMURA, T., K. TANINO, and I. KUWAJIMA. "ChemInform Abstract: Highly Stereoselective Chelation Controlled Ene-Reaction of 2-( Alkylthio)allyl Silyl Ethers." ChemInform 24, no. 29 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199329055.

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29

Chang, Chu-An, Stefan Gürtzgen, Erik P. Johnson, and K. Peter C. Vollhardt. "Stoichiometric and Catalytic (η 5-Cyclopentadienyl)cobalt-Mediated Cycloisomerizations of Ene-Yne-Ene Type Allyl Propargyl Ethers." Synthesis 52, no. 03 (October 28, 2019): 399–416. http://dx.doi.org/10.1055/s-0039-1690727.

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The complexes CpCoL2 (Cp = C5H5; L = CO or CH2=CH2) mediate the cycloisomerizations of α,δ,ω-enynenes containing allylic ether linkages to 3-(oxacyclopentyl or cycloalkyl)furans via the intermediacy of isolable CpCo-η 4-dienes. A suggested mechanism comprises initial complexation of the triple bond and one of the double bonds, then oxidative coupling to a cobalt-2-cyclopentene, terminal double bond insertion to assemble a cobalta-4-cycloheptene, β-hydride elimination, and reductive elimination to furnish a CpCo-η 4-diene. When possible, the cascade continues through cobalt-mediated hydride shifts and dissociation of the aromatic furan ring. The outcome of a deuterium labeling experiment supports this hypothesis. The reaction exhibits variable stereoselectivity with a preference for the trans-product (or, when arrested, its syn-Me CpCo-η 4-diene precursor), but is completely regioselective in cases in which the two alkyne substituents are differentiated electronically by the presence or absence of an embedded oxygen. Regioselectivity is also attained by steric discrimination or blocking one of the two possible β-hydride elimination pathways. When furan formation is obviated by such regiocontrol, the sequence terminates in a stable CpCo-η 4-diene complex. The conversion of the cyclohexane-fused substrate methylidene-2-[5-(2-propenyloxy)-3-pentynyl]cyclohexane into mainly 1-[(1R*,3aS*,7aS*)-7a-methyloctahydroinden-1-yl]-1-ethanone demonstrates the potential utility of the method in complex synthesis.

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Kucharska, MAŁGORZATA, and Wiktor Wesołowski. "1,2-Dimethoxyethane Determination in working air with gas chromatography-mass spectrometer." Podstawy i Metody Oceny Środowiska Pracy 33, no. 2(92) (June 29, 2017): 133–47. http://dx.doi.org/10.5604/01.3001.0010.0062.

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Under normal conditions, 1,2-dimethoxyethane (DME) is a colorless and transparent liquid with a faint odor of ether, very soluble in water, charac-terized by a high vapor pressure. It belongs to the group of alkyl ethers solvents, derivatives of eth-ylene glycol. 1,2-Dimethoxyethane is used as an ex-cipient in preparing and processing industrial chemicals, in the production of fluoric polymers and as a solvent and cleaning agent in the microe-lectronics and printing industries. In the literature there are no data on the acute and chronic toxicity of 1,2-dimethoxyethane. However, long-term epidemiological studies on compounds of similar chemical structure suggest that human exposure to ethylene glycol alkyl ethers can ad-versely affect fertility and fetal development, and hematological parameters. The aim of this study was to develop and validate a sensitive method for determining concentrations of 1,2-dimethoxyethane in workplace air in the range from 1/20 to 2 MAC values, in accordance with the requirements of Standard No. PN-EN 482+A1: 2016-1. The study was performed using a gas chromato-graph (GC). A 7890B Agilent Technologies gas chromatograph with a 5977A mass spectrometry detector (MSD), HP PONA (50 m; 0,2 mm; 0,5 μm) capillary analytical column, auto sampler and Mass Hunter software was used for chromato-graphic separations. The method is based on the adsorption of 1,2-di-methoxyethane on charcoal, desorption with di-chloromethane and GC/MSD analysis of the re-sulting solution. Extraction efficiency of 1,2-di-methoxyethane from charcoal was 96.4%. Samples of 1,2-dimethoxyethane can be stored in refrigera-tor for up to 28 days. The use of a HP-PONA capil-lary column enabled selective determination of 1,2-dimethoxyethane in a mixture of dichloromethane, toluene, carbon disulfide, ethylene and propylene glycol and other compounds. The method is linear (r = 0.9999) within the inves-tigated working range from 5 to 200 μg/ml, which is equivalent to air concentrations from 0.5 to 20 mg/m3 for a 10-L air sample. The limit of quan-tification (LOQ) is 1,306 μg/ml. The analytical method described in this paper ena-bles selective determination of 1,2-dimethoxye-thane in workplace atmosphere in presence of other compounds at concentrations from 0.5 to 20 mg/m3 (1/20 ÷ 2 MAC value). The method is precise, accurate and it meets the criteria for proce-dures for measuring chemical agents listed in Standard No. PN-EN 482+A1: 2016-1. The method can be used for assessing occupational exposure to 1,2-dimethoxyethane and associated risk to work-ers’ health. The developed method of determining 1,2-di-methoxyethane has been recorded as an analytical procedure (see Appendix).

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Magaña-Vergara, Nancy E., Delia Soto-Castro, Hugo Vazquez-Lima, Rebeca Yépez, and Rosa Santillan. "Synthesis of Fréchet-type poly(aryl ether) dendrimers with allyl end groups: comparative convergent and divergent approaches." Arkivoc 2017, no. 5 (July 23, 2017): 117–28. http://dx.doi.org/10.24820/ark.5550190.p009.994.

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Ruths, Marina, and Steve Granick. "Rate-Dependent Adhesion between Opposed Perfluoropoly(alkyl ether) Layers: Dependence on Chain-End Functionality and Chain Length." Journal of Physical Chemistry B 102, no. 31 (July 1998): 6056–63. http://dx.doi.org/10.1021/jp981326l.

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TANINO, K., T. NAKAMURA, and I. KUWAJIMA. "ChemInform Abstract: Highly Threo-Selective Ene-Reaction of 2-(Alkylthio)allyl Silyl Ethers with Aldehydes." ChemInform 22, no. 11 (August 23, 2010): no. http://dx.doi.org/10.1002/chin.199111054.

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34

K. Madhup, Mukesh, Nisha K. Shah, and Neha R. Parekh. "An Investigation of Abrasion Resistance Property of Clay- Epoxy Nanocomposite Coating." Material Science Research India 15, no. 2 (July 7, 2018): 165–78. http://dx.doi.org/10.13005/msri/150209.

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Diglycidyl ether of bisphenol A based epoxy resin was loaded with alkyl quaternary ammonium modified bentonite clay nanoparticles (b-CNPs) in various concentrations. The abrasion resistance (Taber) property of the composite coatings cured with amine were investigated after 7 days and with 60 days curing at two different cycle viz. 500 and 1000. The mass losses of the materials revealed the fact that abrasion resistance increases with increase in CNPs concentration inside epoxy matrix with ageing. Thermal (DSC), spectroscopic (FTIR) and morphological (SEM) studies were performed to characterize the developed epoxy nanocomposite (ENC) coating. A gradual decrease in glass transition temperature (Tg) was observed with increase in the b-CNPs concentration. The modified b-CNPs found interacting with epoxy matrix and the intensity found increasing with increase in b-CNPs concentration during spectroscopic study. Smooth film morphology was revealed by scanning electron microscopic analysis confirming the uniform dispersion of b-CNPs inside polymer nanocomposite matrix.

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35

Desilva, AN, CL Francis, and AD Ward. "Grignard Addition Reactions to 1,4-Difunctionalized But-2-ynes." Australian Journal of Chemistry 46, no. 11 (1993): 1657. http://dx.doi.org/10.1071/ch9931657.

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Trisubstituted alkenes of E geometry have been prepared by anti addition of Grignard reagents to 1,4-difunctionalized but-2-ynes. Addition of primary, secondary and aromatic Grignard reagents to but-2-yne-1,4-diol provided (E)-2-substituted but-2-ene-1,4-diols as major products along with the corresponding 2-substituted buta-2,3-dien-1-ols. Addition of phenylmagnesium bromide to the mono- and di-methyl ethers of but-2-yne-1,4-diol gave 2,3-diphenyl-1,3-diene. Treatment of 4-dimethylaminobut-2-yn-1-ol with primary alkyl and alkenyl Grignard reagents afforded the 2-substituted anti addition product regiospecifically, stereospecifically and in high yield. Reaction of 1-dimethylamino-4-methoxybut-2-yne with butylmagnesium bromide provided only the 3-substituted anti addition product in good yield.

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36

Hon, Yung-Son, and Ying-Chieh Wong. "Synthetic applications of the amine-base treatment in the ozonolysis of substituted-allyl silyl ethers or -allyl esters via a novel ene–diol type rearrangement." Tetrahedron Letters 46, no. 8 (February 2005): 1365–68. http://dx.doi.org/10.1016/j.tetlet.2004.12.135.

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37

Fu, Wen, Li Wang, and Jingwei He. "Evaluation of mechanical properties and shrinkage stress of thiol-ene-methacrylate dental composites with synthesized fluorinated allyl ether." Journal of the Mechanical Behavior of Biomedical Materials 95 (July 2019): 53–59. http://dx.doi.org/10.1016/j.jmbbm.2019.03.027.

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38

He, Min, and Qiuyu Zhang. "Application of Ammonium α-Allyl Alkyl Phenol Polyoxyethylene Ether Sulfonate in Acrylic Emulsion Pressure-Sensitive Adhesive." Polymer-Plastics Technology and Engineering 50, no. 15 (November 2011): 1570–75. http://dx.doi.org/10.1080/03602559.2011.603788.

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39

Sangermano, M., R. Bongiovanni, G. Malucelli, A. Priola, A. Harden, and N. Rehnberg. "Synthesis of new fluorinated allyl ethers for the surface modification of thiol-ene ultraviolet-curable formulations." Journal of Polymer Science Part A: Polymer Chemistry 40, no. 15 (June 19, 2002): 2583–90. http://dx.doi.org/10.1002/pola.10349.

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40

Tan, Ayse, Ayse Sahin Yaglioglu, Nurhan Horasan Kishali, Ertan Sahin, and Yunus Kara. "Evaluation of Cytotoxic Potentials of Some Isoindole-1, 3-Dione Derivatives on HeLa, C6 and A549 Cancer Cell Lines." Medicinal Chemistry 16, no. 1 (January 16, 2020): 69–77. http://dx.doi.org/10.2174/1573406415666181206115638.

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Objective: Considering this information, firstly, isoindole derivatives containing different functional groups 4-13 have been synthesized from 2-alkyl/aryl-3a, 4,7,7a-tetrahydro-1H-isoindole-1, 3(2H)-dione. Background: Norcantharimides are known as norcantharidine derivatives and contain an isoindole skeleton structure. Isoindole derivatives have positive effect on inflammatory pathologies including cancers. Methods: For the synthesis of all compounds, 2-alkyl/aryl-3a, 4,7,7a-tetrahydro-1H-isoindole- 1,3(2H)-dione was used as the starting compound. The syntheses were based on two main reactions: Ene-reaction of singlet oxygen and epoxidation. Secondly, their anticancer activities were evaluated against HeLa, C6 and A549 cancer cell lines by the BrdU assay. Results: Anticancer activities of synthesized compounds (4-13) and 5-FU (5-Florouracil) against HeLa, C6 and A549 cells were investigated at four concentrations (100, 50, 25 and 5 μM). IC50 values of compounds 4-13 were calculated for all cancer cell lines. The investigated compounds showed anticancer activity against the cancer cell lines depending on doses. Compound 7 containing azide and silyl ether exhibited higher inhibitory activity than the other compounds and 5-FU against A549 cancer cell lines (IC50 =19.41± 0.01 μM). Compounds 9 and 11 were determined to exhibit cell-selective activity against HeLa cancer cell lines. Compound 11 had higher activity than the positive control at 100 μM concentrations against C6 cancer cell lines. Conclusion: According to the results observed, isoindole derivatives 7, 9, and 11 might be good potential anticancer agents for the treatment of cervical and glioma cancer due to their antiproliferative properties, having less cytotoxic effects on healthy cells. In addition, compound 7 could be used in in vivo studies of all three-cancer cell lines (C6, HeLa, and A549).

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Maeda, Satoshi, Tomoyo Mohri, Tsubasa Inoue, Yoshio Asano, Yurika Otoki, Masaru Enomoto, Kiyotaka Nakagawa, Shigefumi Kuwahara, and Yusuke Ogura. "Synthesis of a plasmenylethanolamine." Bioscience, Biotechnology, and Biochemistry 85, no. 6 (March 11, 2021): 1383–89. http://dx.doi.org/10.1093/bbb/zbab037.

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ABSTRACT A concise synthesis of a plasmenylethanolamine (PlsEtn-[16:0/18:1 n-9]), known as antioxidative phospholipids commonly found in cell membranes, has been achieved from an optically active known diol through 8 steps. The key transformations for the synthesis of PlsEtn-[16:0/18:1 n-9] are (1) regio- and Z-selective vinyl ether formation via the alkylation of a lithioalkoxy allyl intermediate with an alkyl iodide, and (2) a one-pot phosphite esterification–oxidation sequence to construct the ethanolamine phosphonate moiety in the presence of the vinyl ether functionality. The piperidine salt of synthetic PlsEtn-[16:0/18:1 n-9] was desalinated through reversed-phase high-performance liquid chromatography purification.

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Patrickios, Costas S., Clive Forder, Steven P. Armes, and Norman C. Billingham. "Near-monodisperse,n-alkyl, end-functionalized poly(methyl vinyl ether)s: Synthesis by living cationic polymerization and solution characterization." Journal of Polymer Science Part A: Polymer Chemistry 36, no. 14 (October 1998): 2547–54. http://dx.doi.org/10.1002/(sici)1099-0518(199810)36:14<2547::aid-pola13>3.0.co;2-i.

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43

Tian, Juan, Dayong Sang, Xiaodong Tu, Zhoujun He, and Ming Yao. "Cleavage of Catechol Monoalkyl Ethers by Aluminum Triiodide–Dimethyl Sulfoxide." Synthesis 51, no. 03 (September 26, 2018): 704–12. http://dx.doi.org/10.1055/s-0037-1610996.

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Using eugenol and vanillin as model substrates, a practical method is developed for the cleavage o-hydroxyphenyl alkyl ethers. Aluminum oxide iodide (O=AlI), generated in situ from aluminum triiodide and dimethyl sulfoxide, is the reactive ether cleaving species. The method is applicable to catechol monoalkyl ethers as well as normal phenyl alkyl ethers for the removal of methyl, ethyl, isopropyl, and benzyl groups. A variety of functional groups such as alkenyl, allyl, amide, cyano, formyl, keto, nitro, and halogen are well tolerated under the optimum conditions. Partial hydrodebromination was observed during the demethylation of 4-bromoguaiacol, and was resolved using excess DMSO as an acid scavenger. This convenient and efficient procedure would be a practical tool for the preparation of catechols.

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44

Akhmetvaleev, R. R., L. R. Imaeva, T. A. Belogaeva, and M. S. Miftakhov. "A novel variant for the preparation of allyl(propargyl) vinyl ethers and their rearrangement into 5-allyl(allenyl)-5-chloro-2-(2-hydroxyethyloxy)-cyclopent-2-ene-1,4-diones." Russian Chemical Bulletin 46, no. 11 (November 1997): 1963–64. http://dx.doi.org/10.1007/bf02503796.

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45

Zaragoza-Galicia, Ivann, Zaira A. Santos-Sánchez, Yazmín I. Hidalgo-Mercado, Horacio F. Olivo, and Moisés Romero-Ortega. "Synthesis of 5-Substituted 2-Pyrrolidinones by Coupling of Organozinc Reagents with Cyclic N-Acyliminium Ions." Synthesis 51, no. 24 (October 8, 2019): 4650–56. http://dx.doi.org/10.1055/s-0037-1610733.

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A coupling reaction between cyclic N-acyliminium ions with organozinc reagents is described. The cyclic N-acyliminium ions, generated in situ from N-substituted-5-hydroxy-2-pyrrolidinones by treatment with boron trifluoride–diethyl ether complex or titanium tetrachloride, are trapped by the organozinc reagent, which is formed from an alkyl bromide in the presence of zinc in the same reaction medium. The N-substituted-5-allyl-2-pyrrolidinones generated using this method serve as versatile intermediates for the synthesis of azabicyclic systems with indolizidine and pyrroloazepinolizidine cores.

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46

Kalinova, Radostina, Miroslava Valchanova, Ivaylo Dimitrov, Sevdalina Turmanova, Iva Ugrinova, Maria Petrova, Zlatina Vlahova, and Stanislav Rangelov. "Functional Polyglycidol-Based Block Copolymers for DNA Complexation." International Journal of Molecular Sciences 22, no. 17 (September 4, 2021): 9606. http://dx.doi.org/10.3390/ijms22179606.

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Gene therapy is an attractive therapeutic method for the treatment of genetic disorders for which the efficient delivery of nucleic acids into a target cell is critical. The present study is aimed at evaluating the potential of copolymers based on linear polyglycidol to act as carriers of nucleic acids. Functional copolymers with linear polyglycidol as a non-ionic hydrophilic block and a second block bearing amine hydrochloride pendant groups were prepared using previously synthesized poly(allyl glycidyl ether)-b-polyglycidol block copolymers as precursors. The amine functionalities were introduced via highly efficient radical addition of 2-aminoethanethiol hydrochloride to the alkene side groups. The modified copolymers formed loose aggregates with strongly positive surface charge in aqueous media, stabilized by the presence of dodecyl residues at the end of the copolymer structures and the hydrogen-bonding interactions in polyglycidol segments. The copolymer aggregates were able to condense DNA into stable and compact nanosized polyplex particles through electrostatic interactions. The copolymers and the corresponding polyplexes showed low to moderate cytotoxicity on a panel of human cancer cell lines. The cell internalization evaluation demonstrated the capability of the polyplexes to successfully deliver DNA into the cancer cells.

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47

Witzke, N. M., and R. Bittman. "Convenient synthesis of racemic mixed-chain ether glycerophosphocholines from fatty alkyl allyl ethers: useful analogs for biophysical studies." Journal of Lipid Research 27, no. 3 (January 1987): 344–51. http://dx.doi.org/10.1016/s0022-2275(20)38840-4.

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48

Mosey, Robert A., Jason S. Fisk, Timothy L. Friebe, and Jetze J. Tepe. "Synthesis oftert-Alkyl Amino Hydroxy Carboxylic Esters via an Intermolecular Ene-Type Reaction of Oxazolones and Enol Ethers." Organic Letters 10, no. 5 (March 2008): 825–28. http://dx.doi.org/10.1021/ol702941f.

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49

AKHMETVALEEV, R. R., L. R. IMAEVA, T. A. BELOGAEVA, and M. S. MIFTAKHOV. "ChemInform Abstract: A Novel Variant for the Preparation of Allyl(propargyl) Vinyl Ethers and Their Rearrangement into 5-Allyl(allenyl)-2- (2-hydroxyethyloxy)-5-chlorocyclopent-2-ene-1,4-diones." ChemInform 29, no. 11 (June 23, 2010): no. http://dx.doi.org/10.1002/chin.199811097.

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50

Hanessian, Stephen, Hubli Prabhanjan, Dongxu Qiu, and Sudhir Nambiar. "Synthesis of chemically and functionally diverse scaffolds from pentaerythritol." Canadian Journal of Chemistry 74, no. 9 (September 1, 1996): 1731–37. http://dx.doi.org/10.1139/v96-191.

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Pentaerythritol (2,2-bis-hydroxymethyl-propane-1,3-diol) was converted into a series of mono-, di-, and trisubstituted derivatives, comprising allyl ethers and amino-alkyl ethers, by systematic chemical manipulation of the hydroxy groups. The remaining hydroxymethyl group in the case of the trisubstituted analog was functionalized with ether groups bearing terminal ω-carboxyl or ω-alkene groups. These derivatives are versatile templates and scaffolds for single, double, or triple substitution with appropriate ligands forming amides and esters, and allowing the attachment of the ω-alkene or ω-carboxyl group to solid support for combinatorial chemistry. Key words: molecular diversity, scaffolds, templates and tris(2-aminoethyl)-pentaerythritol.

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