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Artykuły w czasopismach na temat „Sulfoxides”

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Autor: Grafiati

Data publikacji: 4 czerwca 2021

Data aktualizacji: 1 sierpnia 2024

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1

Kimura, Tsutomu, Koto Sekiguchi, Akane Ando i Aki Imafuji. "Fritsch–Buttenberg–Wiechell rearrangement of magnesium alkylidene carbenoids leading to the formation of alkynes". Beilstein Journal of Organic Chemistry 17 (28.05.2021): 1352–59. http://dx.doi.org/10.3762/bjoc.17.94.

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A series of 1-heteroatom-substituted vinyl p-tolyl sulfoxides were prepared and treated with organometallic reagents to evaluate which combination of sulfoxides and organometallic reagents yielded alkynes the most efficiently. The use of 1-chlorovinyl p-tolyl sulfoxide and isopropylmagnesium chloride was optimal for this purpose. A variety of 1-chlorovinyl p-tolyl sulfoxides were prepared from carbonyl compounds and chloromethyl p-tolyl sulfoxide and were converted into alkynes via the sulfoxide/magnesium exchange reaction and subsequent Fritsch–Buttenberg–Wiechell (FBW) rearrangement of the resulting magnesium alkylidene carbenoids. The mechanism of the FBW rearrangement of magnesium alkylidene carbenoids was studied by using 13C-labeled sulfoxides and by using DFT calculations.

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2

Kou, K. G. M., i V. M. Dong. "Tandem rhodium catalysis: exploiting sulfoxides for asymmetric transition-metal catalysis". Organic & Biomolecular Chemistry 13, nr 21 (2015): 5844–47. http://dx.doi.org/10.1039/c5ob00083a.

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Sulfoxides are uncommon substrates for transition-metal catalysis due to their propensity to inhibit catalyst turnover. We have developed the first DKR of racemic allylic sulfoxides where rhodium catalyzed both sulfoxide epimerization and alkene hydrogenation.

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3

Salom-Roig, Xavier, i Claude Bauder. "Recent Applications in the Use of Sulfoxides as Chiral Auxiliaries for the Asymmetric Synthesis of Natural and Biologically Active Products". Synthesis 52, nr 07 (27.01.2020): 964–78. http://dx.doi.org/10.1055/s-0039-1690803.

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The contribution of chiral sulfoxides as versatile auxiliaries in the field of organic chemistry has shown a prevalent interest in the asymmetric synthesis of natural products during the last 45 years. In this short review, we report the recent applications of these chiral auxiliaries to the synthesis of natural and biological active products highlighted from 2010 to 2019. We hope to allow the reader to have an overview of the potential of sulfoxide chemistry in the field of enantioselective synthesis.1 Introduction2 Diastereoselective Additions to Ketones2.1 Reduction of β-Keto Sulfoxides2.2 Reduction of β-Keto Sulfoxides Followed by Bromohydrin Forma tion3 Synthesis of an α-Amino α′-Sulfinyl Ketone Followed by Diastere oselective Reduction of the β-Keto Sulfoxide4 Diastereoselective Addition of Carbanionic Chiral Sulfoxides4.1 Addition to an Aldehyde4.1.1 Aldol Reactions4.1.2 Reformatsky-Type Reactions4.2 Additions to Chiral Sulfinimines5 Diastereoselective Cyclization Reactions Directed by a Chiral Sulf oxide5.1 1,4-Radical Additions5.2 Intramolecular Conjugate Additions5.3 Nazarov Cyclizations5.4 Diels–Alder Reactions6 Atropodiastereoselective Synthesis7 Conclusion

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4

S. Kadam, Satwashila, Niranjan S. Mahajan, Pankaj A. Jadhav i Shashikant C. Dhawale. "SULFOXIDES AND SULFONES: REVIEW". Indian Drugs 60, nr 02 (2.03.2023): 7–14. http://dx.doi.org/10.53879/id.60.02.12267.

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It has been established that sulfoxide with sulfones have distinct pharmacological effects. Commodity compounds like sulfoxide and sulfones find widespread use in many chemical disciplines. This is why organic chemists find the synthesis of sulfoxide and sulfones so interesting. In the process of oxidation, sulphides can transform into sulfoxides or sulfones. Comprehensive oxidation to the sulfones is significantly simpler than mild oxidation to the sulfoxide, but both can be achieved by the use of highly selective technologies.

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5

Tomkiel, Aneta M., Dorota Czajkowska-Szczykowska, Ewa Olchowik-Grabarek, Lucie Rárová, Szymon Sękowski i Jacek W. Morzycki. "A Study on the Chemistry and Biological Activity of 26-Sulfur Analogs of Diosgenin: Synthesis of 26-Thiodiosgenin S-Mono- and Dioxides, and Their Alkyl Derivatives". Molecules 28, nr 1 (26.12.2022): 189. http://dx.doi.org/10.3390/molecules28010189.

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A chemoselective procedure for MCPBA oxidation of 26-thiodiosgenin to corresponding sulfoxides and sulfone was elaborated. An unusual equilibration of sulfoxides in solution was observed. Moreover, α-alkylation of sulfoxide and sulfone was investigated. Finally, the biological activity of obtained compounds was examined.

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6

Holland, Herbert L., Cynthia G. Rand, Peter Viski i Frances M. Brown. "Microbial oxidation of benzyl sulfides and bibenzyl by Mortierella isabellina and Helminthosporium species". Canadian Journal of Chemistry 69, nr 12 (1.12.1991): 1989–93. http://dx.doi.org/10.1139/v91-287.

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The biotransformation of 1,2-diphenylethane by the fungus Mortierella isabellina ATCC 42613, and that of a series of alkyl benzyl sulfides by the fungi M. isabellina and Helminthosporium species NRRL 4671 have been studied. Mortierella hydroxylates 1,2-diphenylethane in low yield, giving (S)-1,2-diphenylethanol with an enantiomeric purity of 33%. Bioconversions of deuterium-labelled and racemic 1,2-diphenylethanol by M. isabellina demonstrate that this organism performs reversible oxidation/reduction of the alcohol. Biotransformations of n-alkyl benzyl sulfides by H. species give predominantly the (S) enantiomer of sulfoxide, with no sulfone formation, but M. isabellina, although showing a general preference for the oxidation of alkyl benzyl sulfides to (R) sulfoxides, also generates sulfones from n-alkyl benzyl sulfides in a time-dependent manner that suggests a stereoselective removal of (R) sulfoxide. The latter microorganism can be used, however, for the production of (R)-benzyl methyl and benzyl isopropyl sulfoxides, and gives (S)-benzyl tert-butyl sulfoxide in low yield. Key words: biotransformation, enzymes, sulfoxides.

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7

Massa, Antonio, Laura Capozzolo i Arrigo Scettri. "Sulfoxides in the allylation of aldehydes in the presence of silicon tetrachloride and allyltributylstannane". Open Chemistry 8, nr 6 (1.12.2010): 1210–15. http://dx.doi.org/10.2478/s11532-010-0099-7.

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AbstractSiCl4 can be conveniently activated by catalytic amounts of dimethyl sulfoxide or other readily-available sulfoxides for the allylation of aromatic, hetero-aromatic and unsaturated aldehydes in the presence of allyltributyl stannane. Chiral aryl methyl sulfoxides have been used to develop asymmetric allylation methods, as well as probe the aldehyde substrate scope.

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8

Somogyi, László. "Elimination, ring-contraction, and fragmentation reactions of 1-thioflavanone 1-oxides". Canadian Journal of Chemistry 79, nr 7 (1.07.2001): 1159–65. http://dx.doi.org/10.1139/v01-096.

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Epimeric thioflavanone sulfoxides (2b) were selectively transformed into thioflavone (1a), thioaurone (3a), and di(2-cinnamoylphenyl) disulfide (4). Disulfide 4 can be recyclized into thioaurones (3ac) and thioflavanones (2a,5) with heterolysis of the SS bond. The 3-p-anisylidene sulfoxide analog of 2b (6) transforms, with fragmentation, into 4'-methoxythioaurone 3b.Key words: chalcone, ring contraction, sulfoxides, thioaurones, thioflavonoids.

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9

Holland, Herbert L., i Benito Munoz. "Fungal biotransformation of 1,3-oxathiolanes". Canadian Journal of Chemistry 66, nr 9 (1.09.1988): 2299–303. http://dx.doi.org/10.1139/v88-364.

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A series of 2,2-disubstituted 1,3-oxathiolanes has been incubated with fungi known to be capable of efficient asymmetric oxidation of sulfides to sulfoxides. In three cases (2-phenyl-1,3-oxathiolane, 2-methyl-2-phenyl-1,3-oxathiolane, and 2-tert-butyl-2-phenyl-1,3-oxathiolane), sulfoxidation occurred to give a single diastereomer of sulfoxide, whose relative stereochemistry has been assigned by 1H nuclear magnetic resonance analysis. The sulfoxides were obtained as racemates or had low enantiomeric enrichment. In some cases ketones, assumed to be formed by spontaneous hydrolysis of oxathiolane sulfoxides, were obtained, together with their reduction products, secondary alcohols.

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10

Hrudková, Hana, Pavel Čefelín i Václav Janout. "Polymer sulfoxides based on poly(vinyl alcohol) as effective catalysts of nucleophilic substitution reactions". Collection of Czechoslovak Chemical Communications 52, nr 9 (1987): 2204–11. http://dx.doi.org/10.1135/cccc19872204.

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Using the addition of alcohols to ethyl vinyl sulfoxide, a number of 2-alkoxyethyl ethyl sulfoxides were prepared, containing the following alkyls: methyl, ethyl, isopropyl, benzyl, and cyclohexyl. With a 10 mole % excess of alcohol the extent of the reaction was 70-95%. By a polymeranalogous reaction with poly(vinyl alcohol) and poly(ethylene-co-vinyl alcohol), copolymers poly[1-hydroxyethylene (74 mole %)-co-1-(2-ethylsulfinylethoxy)ethylene (26 mole %)] and poly[ethylene (62 mole %)-co-1-hydroxyethylene (35 mole %)-co-1-(2-ethylsulfinylethoxy)ethylene (3 mole %)] were prepared; the reaction with polymer alcohols requires the use of excess ethyl vinyl sulfoxide. These polymer sulfoxides were tested as catalysts of nucleophilic substitution reactions, using reactions of 1-bromooctane with sodium phenoxide, sodium iodide and potassium thiocyanate. They are more effective catalysts than polymer sulfoxides based on crosslinked poly(styrene) under the conditions of a two-phase (S-L) and three-phase (L-S-L) catalysis.

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11

Du, Ke-Si, i Jing-Mei Huang. "Electrochemical synthesis of methyl sulfoxides from thiophenols/thiols and dimethyl sulfoxide". Green Chemistry 20, nr 6 (2018): 1405–11. http://dx.doi.org/10.1039/c7gc03864j.

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12

Yoshimoto, Naoko, i Kazuki Saito. "S-Alk(en)ylcysteine sulfoxides in the genus Allium: proposed biosynthesis, chemical conversion, and bioactivities". Journal of Experimental Botany 70, nr 16 (18.05.2019): 4123–37. http://dx.doi.org/10.1093/jxb/erz243.

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Abstract S-Alk(en)ylcysteine sulfoxides are sulfur-containing natural products characteristic of the genus Allium. Both the flavor and medicinal properties of Allium plants are attributed to a wide variety of sulfur-containing compounds that are generated from S-alk(en)ylcysteine sulfoxides. Previous radiotracer experiments proposed that S-alk(en)ylcysteine sulfoxides are biosynthesized from glutathione. The recent identification of γ-glutamyl transpeptidases and a flavin-containing S-oxygenase involved in the biosynthesis of S-allylcysteine sulfoxide (alliin) in garlic (Allium sativum) provided insights into the reaction order of deglutamylation and S-oxygenation together with the localization of the biosynthesis, although the rest of the enzymes in the pathway still await discovery. In intact plants, S-alk(en)ylcysteine sulfoxides are stored in the cytosol of storage mesophyll cells. During tissue damage, the vacuolar enzyme alliinase contacts and hydrolyzes S-alk(en)ylcysteine sulfoxides to produce the corresponding sulfenic acids, which are further converted into various sulfur-containing bioactive compounds mainly via spontaneous reactions. The formed sulfur-containing compounds exhibit bioactivities related to pathogen defense, the prevention and alleviation of cancer and cardiovascular diseases, and neuroprotection. This review summarizes the current understanding of the occurrence, biosynthesis, and alliinase-triggered chemical conversion of S-alk(en)ylcysteine sulfoxides in Allium plants as well as the impact of S-alk(en)ylcysteine sulfoxides and their derivatives on medicinal, food, and agricultural sciences.

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13

Nosek, Vladimír, i Jiří Míšek. "Enzymatic kinetic resolution of chiral sulfoxides – an enantiocomplementary approach". Chemical Communications 55, nr 70 (2019): 10480–83. http://dx.doi.org/10.1039/c9cc05470g.

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14

Srinivasan, C., P. Pandarakutty Jegatheesan, S. Rajagopal i N. Arumugam. "Substituent effects in cooxidation: Cr(VI) – oxalic acid – sulfoxides systems". Canadian Journal of Chemistry 65, nr 10 (1.10.1987): 2421–24. http://dx.doi.org/10.1139/v87-403.

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The kinetics of cooxidation of several substituted phenyl methyl sulfoxides and oxalic acid with Cr(VI) have been carried out in the presence of perchloric acid. The reaction is first order each in sulfoxide, oxalic acid, Cr(VI), and H+. The products of oxidation are sulfones and carbon dioxide. Electron-releasing groups in the phenyl ring accelerate the rate while electron-withdrawing groups retard it. The Hammett correlation yields a reaction constant of −0.927 ± 0.08 (r = 0.994) at 313 K. Addition of aluminium nitrate prevents the occurrence of cooxidation. Based on the kinetic information a suitable mechanism has been proposed. Diaryl sulfoxides behave in an analogous manner in the cooxidation.

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15

Anufrieva, N. V., E. A. Morozova, V. V. Kulikova, N. P. Bazhulina, I. V. Manukhov, D. I. Degtev, E. Yu Gnuchikh, A. N. Rodionov, G. B. Zavilgelsky i T. V. Demidkina. "Sulfoxides, Analogues of L-Methionine and L-Cysteine As Pro-Drugs against Gram-Positive and Gram-Negative Bacteria". Acta Naturae 7, nr 4 (15.12.2015): 128–35. http://dx.doi.org/10.32607/20758251-2015-7-4-128-135.

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The problem of resistance to antibiotics requires the development of new classes of broad-spectrum antimicrobial drugs. The concept of pro-drugs allows researchers to look for new approaches to obtain effective drugs with improved pharmacokinetic and pharmacodynamic properties. Thiosulfinates, formed enzymatically from amino acid sulfoxides upon crushing cells of genus Allium plants, are known as antimicrobial compounds. The instability and high reactivity of thiosulfinates complicate their use as individual antimicrobial compounds. We propose a pharmacologically complementary pair: an amino acid sulfoxide pro-drug and vitamin B6 - dependent methionine -lyase, which metabolizes it in the patients body. The enzyme catalyzes the - and -elimination reactions of sulfoxides, analogues of L-methionine and L-cysteine, which leads to the formation of thiosulfinates. In the present work, we cloned the enzyme gene from Clostridium sporogenes. Ionic and tautomeric forms of the internal aldimine were determined by lognormal deconvolution of the holoenzyme spectrum and the catalytic parameters of the recombinant enzyme in the - and -elimination reactions of amino acids, and some sulfoxides of amino acids were obtained. For the first time, the possibility of usage of the enzyme for effective conversion of sulfoxides was established and the antimicrobial activity of thiosulfinates against Gram-negative and Gram-positive bacteria in situ was shown.

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16

Bayat, Ahmad, Mehdi Shakourian-Fard, Nona Ehyaei i Mohammad Mahmoodi Hashemi. "A magnetic supported iron complex for selective oxidation of sulfides to sulfoxides using 30% hydrogen peroxide at room temperature". RSC Adv. 4, nr 83 (2014): 44274–81. http://dx.doi.org/10.1039/c4ra07356h.

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Selective oxidation of sulfides to corresponding sulfoxides using H₂O₂ as a green oxidant at room temperature have been investigated by a magnetic supported iron (iron(ii) acetylacetonate) as an efficient and recyclable heterogeneous catalyst with excellent sulfide conversion and good sulfoxide selectivity.

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17

Adarve-Cardona, Laura, i Diego Gamba-Sánchez. "Reduction of Sulfoxides in Multigram Scale, an Alternative to the Use of Chlorinated Solvents". Processes 10, nr 6 (2.06.2022): 1115. http://dx.doi.org/10.3390/pr10061115.

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In this manuscript, we describe the use of ethyl vinyl ether/oxalyl chloride as the reducing mixture for sulfoxides. The reaction is based on the high electrophilic character of chlorosulfonium salts, formed in situ by the reaction of oxalyl chloride and the sulfoxide. Thereafter, the nucleophilic vinyl ether acts as a chlorine scavenger, affording the corresponding sulfide. The method is applicable on a big scale and may be applied to highly functionalized sulfoxides. Chromatographic purification is only needed in exceptional cases of unstable substrates, and the final sulfide or the corresponding salt is usually obtained after simple evaporation of volatiles. The sole contaminants of this method are carbon dioxide, carbon monoxide and small (five-carbon maximum) aldol products, which are formed during the reaction process.

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18

Madabeni, Andrea, i Laura Orian. "The Key Role of Chalcogenurane Intermediates in the Reduction Mechanism of Sulfoxides and Selenoxides by Thiols Explored In Silico". International Journal of Molecular Sciences 24, nr 9 (24.04.2023): 7754. http://dx.doi.org/10.3390/ijms24097754.

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Sulfoxides and selenoxides oxidize thiols to disulfides while being reduced back to sulfides and selenides. While the reduction mechanism of sulfoxides to sulfides has been thoroughly explored experimentally as well as computationally, less attention has been devoted to the heavier selenoxides. In this work, we explore the reductive mechanism of dimethyl selenoxide, as an archetypal selenoxide and, for the sake of comparison, the reductive mechanism of dimethyl sulfoxide to gain insight into the role of the chalcogen on the reaction substrate. Particular attention is devoted to the key role of sulfurane and selenurane intermediates. Moreover, the capacity of these system to oxidize selenols rather than thiols, leading to the formation of selenyl sulfide bridges, is explored in silico. Notably, this analysis provides molecular insight into the role of selenocysteine in methionine sulfoxide reductase selenoenzyme. The activation strain model of chemical reactivity is employed in the studied reactions as an intuitive tool to bridge the computationally predicted effect of the chalcogen on the chalcogenoxide as well as on the chalcogenol.

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19

Serreqi, Alessio N., i Romas J. Kazlauskas. "Kinetic resolution of sulfoxides with pendant acetoxy groups using cholesterol esterase: substrate mapping and an empirical rule for chiral phenols". Canadian Journal of Chemistry 73, nr 8 (1.08.1995): 1357–67. http://dx.doi.org/10.1139/v95-167.

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Sulfoxides are valuable chiral auxiliaries because they direct the formation of carbon–carbon bonds. As a route to enantiomerically pure sulfoxides, we examined hydrolase-catalyzed kinetic resolution by hydrolysis of a pendant acetoxy group. Screening hydrolases for the enantioselective hydrolysis of the acetate in 2-(methylsulfinyl)phenyl acetate, 1b, identified cholesterol esterase (CE) as the most enantioselective enzyme. The enantiomeric ratio, E, ranged from 10 to 25, favoring the (R) configuration at sulfur. Competing chemical hydrolysis of 1b caused the large range in the measured values of E. A small-scale (250 mg) resolution of (±)-1b yielded (S)-1b with >99% ee (11% yield) after recrystallization. Changing the methyl substituent to phenyl or n-butyl did not significantly change the enantioselectivity (E = 10 and 15, respectively), but changing it to a chloromethyl substituent lowered the enantioselectivity slightly (E = 5). Changing the phenyl acetate to a naphthyl acetate (2-(phenylsulfinyl)phenyl acetate vs. 1-(phenylsulfinyl)-2-naphthyl acetate) increased the enantioselectivity from 10 to 19. In all cases CE favored the (R)-sulfoxide. To aid the design of new resolutions with CE, we propose an empirical rule that accounts for the observed enantiopreference of CE toward these 5 sulfoxides and 15 other chiral aryl acetates. This empirical rule uses both the size of the substituents and their conformational preferences to predict which enantiomer reacts faster. Keywords: kinetic resolution, lipase, cholesterol esterase, sulfoxides, empirical rule.

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20

Haynes, RK, AG Katsifis, LM King i SC Vonwiller. "Aprotic Conjugate Addition Reactions of Lithiated Allylic Sulfoxides With Acyclic Enones; a Breakdown of the trans-Decalyl Transition State". Australian Journal of Chemistry 42, nr 10 (1989): 1785. http://dx.doi.org/10.1071/ch9891785.

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The reactions of lithiated 1-(t-butylsulfinyl)prop-2-ene, 1-(t-butylsulfinyl)-3-methylbut-2-ene, 1-(t-butylsulfinyl)but-2-ene, 1-(phenylsulfinyl)but-2-ene and 2-methyl-1-(phenylsu1finyl)prop- 2-ene with methyl vinyl ketone, mesityl oxide and crotonaldehyde give largely carbonyl addition products arising from reaction through C1 or C3 of the allyl system. In the case of methyl crotonate, conjugate addition through C3 is observed. The initially formed diastereomers of the C1 adducts, allylic sulfoxides, are configurationally unstable. Only the lithiated 1-(t-butylsulfinyl)-3-methylbut-2-ene undergoes conjugate addition with methyl vinyl ketone to give an (E)-vinyl sulfoxide whose formation may involve the trans-decalyl transition state characteristic of the reactions of lithiated allylic sulfoxides with cyclic enones.

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21

Mohammadpoor-Baltork, Iraj, Hamid R. Memarian i Kiumars Bahrami. "3-Carboxypyridinium chlorochromate aluminium chloride An efficient and inexpensive reagent system for the selective oxidation of sulfides to sulfoxides and sulfones in solution and under microwave irradiation". Canadian Journal of Chemistry 83, nr 2 (1.02.2005): 115–21. http://dx.doi.org/10.1139/v05-008.

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3-Carboxypyridinium chlorochromate (CPCC) in the presence of aluminium chloride is a very efficient reagent for the selective oxidation of sulfides to sulfoxide and sulfones in solution and under microwave irradiation. It is noteworthy that different functional groups including carboncarbon double bonds, ketones, oximes, aldehydes, ethers, and acetals were tolerated under these reaction conditions.Key words: sulfoxides, sulfones, oxidation, chlorochromate, Lewis acid.

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22

Lipantyev, R. E., i V. P. Tutubalina. "EFFECT OF PROPELLER MIXER TURNS NUMBER ON THE SULFIDES OXIDATION RATE IN THE OIL PHASE IN A MIXING REACTOR". Proceedings of the higher educational institutions. ENERGY SECTOR PROBLEMS 20, nr 9-10 (24.01.2019): 79–83. http://dx.doi.org/10.30724/1998-9903-2018-20-9-10-79-83.

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The effect of the rotation number of the propeller mixer on the concentration of sulfoxide sulfur in the oil fraction of Arlan oil during the oxidation of this fraction sulfides with hydrogen peroxide along with an acid catalyst, a mixture of formic and sulfuric acids in a mixing reactor, was studied. The dependences of the concentration of sulfoxide sulfur in the oil fraction and the reaction rate of the oxidation of the fraction sulfides to sulfoxides are obtained experimentally depending on the intensity of heterogeneous blend mixing in the blending reactor.

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23

LOCKARD, James, Calvin SCHROECK i Carl JOHNSON. "Synthesis of Optically Active Dialkyl Sulfoxides from Aryl Alkyl Sulfoxides1". Synthesis 1973, nr 08 (12.09.2002): 485–86. http://dx.doi.org/10.1055/s-1973-22237.

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24

Hsu, Fu Lian, Linda L. Szafraniec, William T. Beaudry i Yu Chu Yang. "Oxidation of 2-chloroethyl sulfides to sulfoxides by dimethyl sulfoxide". Journal of Organic Chemistry 55, nr 13 (czerwiec 1990): 4153–55. http://dx.doi.org/10.1021/jo00300a036.

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25

Bonini, Bianca F., Mauro Comes Franchini, Germana Mazzanti, Jan-Willem Slief, Margreth A. Wegman i Binne Zwanenburg. "Sulfoxide induced sigmatropic rearrangement (SISR) of methyl 1-methylsulfanylvinyl sulfoxides". Chemical Communications, nr 11 (1997): 1011–12. http://dx.doi.org/10.1039/a701942d.

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26

Marino, Joseph P., Laura J. Anna, Roberto Fernández de la Pradilla, María Victoria Martínez, Carlos Montero i Alma Viso. "Sulfoxide-controlled SN2′ displacements between cyanocuprates and epoxy vinyl sulfoxides". Tetrahedron Letters 37, nr 44 (październik 1996): 8031–34. http://dx.doi.org/10.1016/0040-4039(96)01817-5.

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27

Shainsky, Janna, Netta-Lee Derry, Yael Leichtmann-Bardoogo, Thomas K. Wood i Ayelet Fishman. "Rapid Methods for High-Throughput Detection of Sulfoxides". Applied and Environmental Microbiology 75, nr 14 (22.05.2009): 4711–19. http://dx.doi.org/10.1128/aem.02674-08.

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ABSTRACT Enantiopure sulfoxides are prevalent in drugs and are useful chiral auxiliaries in organic synthesis. The biocatalytic enantioselective oxidation of prochiral sulfides is a direct and economical approach for the synthesis of optically pure sulfoxides. The selection of suitable biocatalysts requires rapid and reliable high-throughput screening methods. Here we present four different methods for detecting sulfoxides produced via whole-cell biocatalysis, three of which were exploited for high-throughput screening. Fluorescence detection based on the acid activation of omeprazole was utilized for high-throughput screening of mutant libraries of toluene monooxygenases, but no active variants have been discovered yet. The second method is based on the reduction of sulfoxides to sulfides, with the coupled release and measurement of iodine. The availability of solvent-resistant microtiter plates enabled us to modify the method to a high-throughput format. The third method, selective inhibition of horse liver alcohol dehydrogenase, was used to rapidly screen highly active and/or enantioselective variants at position V106 of toluene ortho-monooxygenase in a saturation mutagenesis library, using methyl-p-tolyl sulfide as the substrate. A success rate of 89% (i.e., 11% false positives) was obtained, and two new mutants were selected. The fourth method is based on the colorimetric detection of adrenochrome, a back-titration procedure which measures the concentration of the periodate-sensitive sulfide. Due to low sensitivity during whole-cell screening, this method was found to be useful only for determining the presence or absence of sulfoxide in the reaction. The methods described in the present work are simple and inexpensive and do not require special equipment.

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Holland, Herbert L., Carl D. Turner, Peter R. Andreana i Doan Nguyen. "Article". Canadian Journal of Chemistry 77, nr 4 (1.04.1999): 463–71. http://dx.doi.org/10.1139/v99-068.

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The enantioselective oxidation of a series of heterocyclic prochiral sulfides to chiral sulfoxides has been examined using the fungal biocatalysts Helminthosporium species NRRL 4671 and Mortierella isabellina ATCC 42613. Methylthiofuranyl and -thiophenyl substrates gave (S)-configuration products in low to moderate enantiomeric purity on biotransformation with H. species, but pyridyl sulfides with the nitrogen atom located at an optimal distance of 8-10 Å from the sulfur centre gave (S) sulfoxides of high enantiomeric purity. The biotransformation of appropriately substituted benzothiane substrates by M. isabellina also gave products of high enantiomeric purity, but with (R) configuration at sulfur. The acceptability of the substrate and the configuration of sulfur oxidation by both H. species and M. isabellina for the range of substrates examined were found to be consistent with predictions based on cubic space models for these oxidations.Key words: bioconversion, biotransformation, Helminthosporium, Mortierella isabellina, sulfide, sulfoxide.

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29

Labischinski, Harald, Dieter Naumann, Gerhard Barnickel, Wolfgang Dreißig, Wojciech Gruszecki, Andreas Hofer i Hans Bradaczek. "Comparison between the Molecular and Crystal Structures of a Benzylpenicillin Ester and its Corresponding Sulfoxide with Drastically Reduced Biological Activity". Zeitschrift für Naturforschung B 42, nr 3 (1.03.1987): 367–75. http://dx.doi.org/10.1515/znb-1987-0320.

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A comparative X-ray structure determination was performed to elucidate possible conformational differences between penicillins and penicillin sulfoxides. Penicillin-G-acetoxy-methylester and its β-oxide were used as model substances, because the only chemical difference between both compounds resides in the thiazolidine ring sulfur oxidation. On the basis of the X-ray data as well as of infrared measurements it is discussed that the drastically reduced biological activity of the penicillin-G-sulfoxide might be related to conformational differences in thiazolidine ring puckering or, even more simply, to the geometric position of the sulfoxide oxygen atom, both of which may hamper the proper reaction of the sulfoxide with its target enzyme(s)

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30

Mutalova, Markhamat Akramovna, i Nargiza Abdurasulovna Abdurakhmanova. "The Study Of The Selection Of Lead-Copper Concentrate By The Sulfite Method". American Journal of Applied Sciences 03, nr 03 (25.03.2021): 13–21. http://dx.doi.org/10.37547/tajas/volume03issue03-03.

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Currently, sulfoxide methods are of greatest interest for the practice of separation of lead-copper concentrates. The selection processes based on the use of sulfoxides such as sulfuric acid, sulfite salts, etc. should be included in this subgroup.d. Typically, these reagents are used in combination with other depressors [3]. The main advantage of sulfoxide methods is the lack of dissolution of noble metals and higher efficiency compared to many known methods. The subgroup under consideration includes a method using sodium sulfite, iron vitriol and sulfuric acid for halenite depression Currently, about thirty methods of flotation separation of lead-copper concentrates are known.

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31

Li, Ai-Tao, Jian-Dong Zhang, Jian-He Xu, Wen-Ya Lu i Guo-Qiang Lin. "Isolation of Rhodococcus sp. Strain ECU0066, a New Sulfide Monooxygenase-Producing Strain for Asymmetric Sulfoxidation". Applied and Environmental Microbiology 75, nr 2 (3.10.2008): 551–56. http://dx.doi.org/10.1128/aem.01527-08.

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ABSTRACT A new and efficient sulfide monooxygenase-producing strain, ECU0066, was isolated and identified as a Rhodococcus sp. that could transform phenylmethyl sulfide (PMS) to (S)-sulfoxide with 99% enantiomeric excess via two steps of enantioselective oxidations. Its enzyme activity could be effectively induced by adding PMS or phenylmethyl sulfoxide (PMSO) directly to a rich medium at the early log phase (6 h) of fermentation, resulting in over 10-times-higher production of the enzyme. This bacterial strain also displayed fairly good activity and enantioselectivity toward seven other sulfides, indicating a good potential for practical application in asymmetric synthesis of chiral sulfoxides.

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32

Bhanuchandra, M., Mamta Yadav, Ram Singh Jat i Bibek Sarma. "2-Pyridyl Sulfoxide Directed Pd(II)-Catalyzed C–H Olefination of Arenes with Molecular Oxygen as the Sole Oxidant". Synthesis 53, nr 13 (8.02.2021): 2269–76. http://dx.doi.org/10.1055/a-1385-6119.

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AbstractPd(II)-catalyzed C–H olefination of aryl 2-pyridyl sulfoxides with unactivated and activated olefins has been demonstrated. We employed environmentally benign and inexpensive molecular oxygen as the sole oxidant. The versatile nature of the 2-pyridyl sulfoxide directing group has been proven by its transformation to the sulfone functionality. Deuterium scrambling experiments and intramolecular kinetic isotopic studies were carried out to gain insights into the reaction pathway.

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33

Adam, Waldemar, Frank Heckel, Chantu R. Saha-Möller, Marcus Taupp, Jean-Marie Meyer i Peter Schreier. "Opposite Enantioselectivities of Two Phenotypically and Genotypically Similar Strains of Pseudomonas frederiksbergensis in Bacterial Whole-Cell Sulfoxidation". Applied and Environmental Microbiology 71, nr 4 (kwiecień 2005): 2199–202. http://dx.doi.org/10.1128/aem.71.4.2199-2202.2005.

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ABSTRACT Soil samples were screened to select microorganisms with the capability to oxidize organic sulfides into the corresponding sulfoxides with differential enantioselectivities. Several bacterial strains that preferentially produced the S-configured sulfoxide enantiomer were isolated. Surprisingly, one bacterial strain, genotypically and phenotypically characterized as Pseudomonas frederiksbergensis, selectively gave the R enantiomer. The finding that two apparently identical organisms displayed opposite enantioselectivities is novel for non-genetically modified organisms.

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34

Boyd, Derek R., Narain D. Sharma, John F. Malone, Vera Ljubez, Deirdre Murphy, Steven D. Shepherd i Christopher C. R. Allen. "Chemoenzymatic synthesis of enantiopure hydroxy sulfoxides derived from substituted arenes". Organic & Biomolecular Chemistry 14, nr 9 (2016): 2651–64. http://dx.doi.org/10.1039/c5ob02411k.

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35

Mikolajczyk, Marian, Wanda Midura i Morton Kajtar. "α-PHOSPHORYL SULFOXIDES 7.1CHIROPTICAL PROPERTIES OF α-PHOSPHORYL SULFOXIDES". Phosphorous and Sulfur and the Related Elements 36, nr 1-2 (marzec 1988): 79–84. http://dx.doi.org/10.1080/03086648808079001.

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36

Darvesh, Sultan, Andrew S. Grant, David I. MaGee i Zdenek Valenta. "Synthetic studies towards bruceantin. Part 2. The synthesis of a pentacyclic intermediate". Canadian Journal of Chemistry 69, nr 4 (1.04.1991): 723–31. http://dx.doi.org/10.1139/v91-107.

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In a synthetic approach to the quassinoid bruceantin (2), the key intermediate 8 obtained via alkylation of a dianion has been transformed into the pentacyclic intermediate 33 via an ABDC ring forming strategy. The key steps involved in this route are as follows: a unique acid catalyzed cyclization, 19 → 20; an intramolecular Michael reaction, 24 → 28; and an allyl sulfoxide [2,3]-sigmatropic rearrangement to introduce the axial C12 alcohol, 31 → 33. Key words: bruceantin, quassinoids, cyclization, sulfoxides, sigmatropic rearrangement.

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37

Pu, Qiang, Mosstafa Kazemi i Masoud Mohammadi. "Application of Transition Metals in Sulfoxidation Reactions". Mini-Reviews in Organic Chemistry 17, nr 4 (31.05.2020): 423–49. http://dx.doi.org/10.2174/1570193x16666190430154835.

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Sulfoxides are key scaffolds in the synthesis of pharmaceutically active molecules. A large number of sulfoxides are indispensable ingredients in the structure of most antibiotics, biological and natural products such as Modafinil, Adrafinil, CRL-40,941 or fladrafinil, Fipronil, Oxydemetonmethyl, Omeprazole, Pantoprazole, Lansoprazole and Rabeprazole. The oxidation of sulfides is the most common and efficient strategy for the preparation of sulfoxides. Recently, many protocols based on using transition metals have been reported for the oxidation of sulfides to the sulfoxides. In this paper, we summarized a nice category of the reported protocols in the literature for the oxidation of sulfides to sulfoxides.

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38

Zhong, Ping, Xian Huang i Meng Ping-Guo. "Hydrozirconation of Alkynyl Sulfoxides: the Reactions of Zirconated Vinyl Sulfoxide Intermediates". Tetrahedron 56, nr 45 (listopad 2000): 8921–25. http://dx.doi.org/10.1016/s0040-4020(00)00843-7.

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39

Hampel, Thomas, Simon Ruppenthal, Daniel Sälinger i Reinhard Brückner. "Desymmetrization of Prochiral Diaryl Sulfoxides by an Asymmetric Sulfoxide-Magnesium Exchange". Chemistry - A European Journal 18, nr 11 (22.02.2012): 3136–40. http://dx.doi.org/10.1002/chem.201103928.

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40

Staggs, R. Louis, i William G. Lyon. "FT-IR Solution Spectra of Propyl Sulfide, Propyl Sulfoxide, and Propyl Sulfone". Applied Spectroscopy 49, nr 12 (grudzień 1995): 1772–75. http://dx.doi.org/10.1366/0003702953965911.

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FT-IR spectra were obtained of 0.5% volumetric solutions of propyl sulfide, propyl sulfoxide, and propyl sulfone in hexane, CCl4, CS2, and CHCl3 to assist in the assignment of FT-IR-PAS spectra of propyl sulfoxide sorbed within the structure of several peats and onto cellulose. The C-H stretching bands of all three compounds showed a 10-fold larger solvent sensitivity than did analogous aliphatic bands in a comparable series of n-alkanes in solution. The S=O stretching bands of alkyl sulfoxides are known to be quite sensitive to solvent environments because of donor-acceptor interactions involving the oxygen of the sulfoxide group and the slightly acidic protons of generalized organic acids; the expected decreases in frequency were seen with propyl sulfoxide and acidic solvents like chloroform. The frequencies of asymmetric and symmetric stretching vibrations of the -SO2 group of propyl sulfone both exhibit smaller decreases in Old, than does the sulfoxide S=O stretching vibration.

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41

Trost, Barry M., Michael C. Ryan i Meera Rao. "Chiral cyclopentadienylruthenium sulfoxide catalysts for asymmetric redox bicycloisomerization". Beilstein Journal of Organic Chemistry 12 (7.06.2016): 1136–52. http://dx.doi.org/10.3762/bjoc.12.110.

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A full account of our efforts toward an asymmetric redox bicycloisomerization reaction is presented in this article. Cyclopentadienylruthenium (CpRu) complexes containing tethered chiral sulfoxides were synthesized via an oxidative [3 + 2] cycloaddition reaction between an alkyne and an allylruthenium complex. Sulfoxide complex 1 containing a p-anisole moiety on its sulfoxide proved to be the most efficient and selective catalyst for the asymmetric redox bicycloisomerization of 1,6- and 1,7-enynes. This complex was used to synthesize a broad array of [3.1.0] and [4.1.0] bicycles. Sulfonamide- and phosphoramidate-containing products could be deprotected under reducing conditions. Catalysis performed with enantiomerically enriched propargyl alcohols revealed a matched/mismatched effect that was strongly dependent on the nature of the solvent.

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42

Liang, Hong, Micheline MacKay, T. Bruce Grindley, Katherine N. Robertson i T. Stanley Cameron. "Configurations and conformations of glycosyl sulfoxides". Canadian Journal of Chemistry 88, nr 11 (listopad 2010): 1154–74. http://dx.doi.org/10.1139/v10-091.

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X-ray crystallographic studies of two axial glycosyl sulfoxides having RS configurations (derivatives of phenyl 2-azido-2-deoxy-1-thio-α-d-galactopyranoside S-oxide) show that they adopt anti conformations in the solid state, in contrast to previous observations and assumptions. Density functional theory (DFT) calculations at the B3lYP6–311G+(d,p)/6–31G(d) level confirm that anti conformations of both phenyl and methyl RS glycosyl sulfoxides of 2-azido-2-deoxy-α-d-pyranosides are more stable than exo-anomeric conformations in the gas phase. 1D NOE measurements indicate that the more polar exo-anomeric conformers are only populated to a slight extent in solution. The anti conformations are distorted so that the glycosyl substituents are closer to being eclipsed with H1. This distortion allows S n → σ* overlap if the sulfur lone pair is a p-type lone pair. Evidence for this overlap comes from short C1–S bond distances, as short as the comparable bond distances in the X-ray crystal structure and in the results from DFT calculations for the SS glycoside, which does adopt the expected exo-anomeric conformation, both in the solid state and in solution, and has normal n → σ* overlap. For 2-deoxy derivatives not bearing a 2-azido group, gas-phase DFT calculations at the same level indicate that the anti- and exo-anomeric conformers have comparable stabilities. Comparison of the results of the two series shows that electronegative substituents in equatorial orientations at C2 destabilize conformations with parallel S–O arrangements, the conformation favored by having an endocyclic C–O dipole antiparallel to the S–O dipole, by about 2.5 kcal mol–1 (1 cal = 4.184 J). An equatorial glycosyl sulfoxide, (SS) phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-d-glucopyranoside S-oxide, also adopts an anti conformation in the solid state as shown by X-ray diffraction. It also adopts this conformation in solution, in contrast to studies of other equatorial glycosyl sulfoxides.

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43

Tureček, František, Libor Brabec, Tomáš Vondrák, Vladimír Hanuš, Josef Hájíček i Zdeněk Havlas. "Sulfenic acids in the gas phase. Preparation, ionization energies and heats of formation of methane-, ethene-, and benzenesulfenic acid". Collection of Czechoslovak Chemical Communications 53, nr 9 (1988): 2140–58. http://dx.doi.org/10.1135/cccc19882140.

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Methane-, ethene-, and ethynesulfenic acids were generated in the gas phase by flash-vacuum pyrolysis of the corresponding tert-butyl sulfoxides at 400 °C and 10-4 Pa. Benzenesulfenic acid was prepared from phenyl 3-buten-1-yl sulfoxide at 350 °C and 10-4 Pa. The sulfenic acids were characterized by mass spectrometry Threshold ionization energies (IE) were measured as IE(CH3SOH) = 9·07 ± 0·03 eV, IE(CH2=CHSOH) = 8·70 ± 0·03 eV, IE(HCCSOH) = 8·86 ± 0·04 eV, and IE(C6H5SOH) = 8·45 + 0·03 eV. Radical cations [CH3SOH].+, [CH2=CHSOH].+, and [HCCSOH].+ were generated by electron-impact-induced loss of propene from the corresponding propyl sulfoxides and their heats of formation were assessed by appearance energy measurements as 685, 824, and 927 kJ mol-1, respectively. Heats of formation of the neutral sulfenic acids and the S-(O) (C), S-(O) (Cd), S-(O) (Ct) and S-(O) (CB) group equivalents were determined. The experimental data, supported by MNDO calculations, point to sulfenate-like structures (R-S-OH) for the sulfenic acids under study.

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44

Sh Bozorova, L., M. J. Qurbanov, O. J. Pirimov i O. Tursunov. "Arenothiophenes in oil basic sulfoxides synthesis and oxidation receiving sulfoxides from oil". IOP Conference Series: Earth and Environmental Science 939, nr 1 (1.12.2021): 012018. http://dx.doi.org/10.1088/1755-1315/939/1/012018.

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Abstract Some of the sulfide compounds were converted to sulfoxides by the action of a 30% solution of hydrogen peroxide on the acid catalyst of a molecule of bicyclic sulfide organic compounds in the paraffin distillate of the oil. The resulting sulfoxides were treated with 70% sulfuric acid and sulfate compounds of sulfoxides were obtained. In order to confirm the composition and structure of these compounds, chemical reactions of the corresponding sulfoxides on the basis of benzothiophene derivatives were carried out.

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45

Strickler, Rick R., John M. Motto, Craig C. Humber i Adrian L. Schwan. "Stereospecific Grignard reactions of cholesteryl 1-alkenesulfinate esters: Application of the Andersen Protocol to the preparation of non-racemic α,β-unsaturated sulfoxides". Canadian Journal of Chemistry 81, nr 6 (1.06.2003): 423–30. http://dx.doi.org/10.1139/v03-002.

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Enantiomerically enriched α,β-unsaturated sulfinate esters of ()-cholesterol undergo stereospecific substitutions at sulfur when treated in benzene at 6°C with Grignard reagents. Sulfoxides with ees of 8599.5% are obtained when enantiopure sulfinates are used. The substitution reactions proceed with inversion of sulfur configuration. Enantiomerically pure cholesteryl (E)-2-carbomethoxyethenesulfinate is not a suitable reactant under the Grignard reaction conditions. It is suggested that the ester group induces unwanted reactions significantly lowering both the yield and sulfur stereogenicity.Key words: sulfinate, sulfoxide, Grignard reagents, stereospecific, unsaturated.

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Ho, Tse-Lok, i C. WONG. "Deoxygenation of Sulfoxides". Synthesis 1973, nr 04 (18.03.2002): 206–7. http://dx.doi.org/10.1055/s-1973-22175.

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Wojaczyńska, Elżbieta, i Jacek Wojaczyński. "Sulfoxides in medicine". Current Opinion in Chemical Biology 76 (październik 2023): 102340. http://dx.doi.org/10.1016/j.cbpa.2023.102340.

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Shiri, Lotfi, i Mosstafa Kazemi. "Deoxygenation of sulfoxides". Research on Chemical Intermediates 43, nr 11 (12.06.2017): 6007–41. http://dx.doi.org/10.1007/s11164-017-2976-6.

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Nakayama, Yuya, Hsin-Jung Ho, Miki Yamagishi, Hiroyuki Ikemoto, Michio Komai i Hitoshi Shirakawa. "Cysteine Sulfoxides Enhance Steroid Hormone Production via Activation of the Protein Kinase A Pathway in Testis-Derived I-10 Tumor Cells". Molecules 25, nr 20 (14.10.2020): 4694. http://dx.doi.org/10.3390/molecules25204694.

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Testosterone plays an important role in male sexual characteristics and maturation, and decreased testosterone levels increase the risk of several diseases. Recently, onion extract rich in cysteine sulfoxides, which are amino acids unique to onions, has been reported to alleviate age-related symptoms resulting from decreased testosterone levels in males. However, the mechanism underlying the suppression of low testosterone levels by cysteine sulfoxides has not been elucidated. In this study, we found that onion extract containing cysteine sulfoxides enhanced progesterone, a precursor of testosterone, in mouse testis-derived I-10 tumor cells. Furthermore, cysteine sulfoxides activated protein kinase A (PKA) and cyclic adenosine monophosphate response element-binding protein, which are key factors in steroidogenesis. These results suggest that cysteine sulfoxides enhance steroid hormone production via activation of the PKA signaling pathway.

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50

Allenmark, Stig, Sofia Claeson i Christina Löwendahl. "Stereochemistry of the formation of endocyclic sulfoximides from o-carboxyphenyl sulfoxides". Tetrahedron: Asymmetry 7, nr 2 (luty 1996): 361–64. http://dx.doi.org/10.1016/0957-4166(96)00006-7.

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