- Iron(II)-induced degradation of antimalarial β-sulfonyl endoperoxides. Evidence for the generation of potentially cytotoxic carbocations
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Reactions of antimalarial β-sulfonyl endoperoxides 9 and 10, which, like yingzhaosu A (2), derive from the 2,3-dioxabicyclo[3.3.1]nonane system 3, with iron(II) salts were studied. Product analysis of the iron(II)-induced degradations provided evidence fo
- Szpilman,Korshin,Hoos,Posner,Bachi
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Read Online
- The facile synthesis of 1-benzoazepine derivatives via gold-catalyzed regioselective cycloisomerization reactions of N-(o-alkynylaryl)-N-vinyl sulfonamides
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Gold-catalyzed, regioselective cycloisomerization of N-(o-alkynylaryl)-N-vinyl sulfonamides afforded high yields of 2-sulfonylmethyl-1-benzoazepine derivatives. This 7-endo-dig selective cyclization proceeds via the incorporation of an exocyclic double bond by a labile 1-benzoazepine intermediate. The cyclization substrates were assembled in two steps from readily available materials using Sonogashira coupling and a Cs2CO3-mediated formal vinylic substitution.
- Undeela, Sridhar,Ravikumar, Gurram,Nanubolu, Jagadeesh Babu,Singarapu, Kiran Kumar,Menon, Rajeev S.
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Read Online
- Iron-Catalyzed, Site-Selective Difluoromethylthiolation (-SCF2H) and Difluoromethylselenation (-SeCF2H) of Unactivated C(sp3)-H Bonds in N-Fluoroamides
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The iron-catalyzed δ-C(sp3)-H bond difluoromethylthiolation and difluoromethylselenation of aliphatic amides with high site selectivity are reported. Essential to the success is the employment of an amide radical formed in situ to activate the inert C(sp3
- Zhang, Hongwei,Yu, Fei,Li, Chuang,Tian, Peiyuan,Zhou, Yulu,Cao, Zhong-Yan
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supporting information
p. 4721 - 4725
(2021/06/28)
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- A mild and chemoselective CALB biocatalysed synthesis of sulfoxides exploiting the dual role of AcOEt as solvent and reagent
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A mild, chemoselective and sustainable biocatalysed synthesis of sulfoxides has been developed exploiting CALB and using AcOEt with a dual role of more environmentally friendly reaction solvent and enzyme substrate. A series of sulfoxides, including the drug omeprazole, have been synthesised in high yields and with excellent E-factors.
- Anselmi, Silvia,Liu, Siyu,Kim, Seong-Heun,Barry, Sarah M.,Moody, Thomas S.,Castagnolo, Daniele
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p. 156 - 161
(2021/01/14)
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- Facile One-Pot Access to α-Diazo-β-ketosulfones from Sulfonyl Chlorides and α-Haloketones
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A convenient one-pot approach to the preparation of α-diazo-β-ketosulfones from sulfonyl chlorides is described. It involves the conversion of the sulfonyl chloride to sodium sulfinate, alkylation of the latter with α-haloketones followed by diazo transfer using the 'sulfonyl-azide-free' ('SAFE') protocol in aqueous medium. The simple and expedient method relies on readily available starting materials and provides facile access to a wide variety of valuable diazo reagents for organic synthesis.
- Dar'In, Dmitry,Kantin, Grigory,Bakulina, Olga,Krasavin, Mikhail
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p. 2259 - 2266
(2020/08/26)
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- Synthesis, Structure, and Chemical Transformations of 2-Chloroprop-2-en-1-yl Sulfones
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A green approach was proposed for the synthesis of 2-chloroprop-2-en-1-yl sulfones in 47–94% yield. The molecular and crystal structures of 2-chloroprop-2-en-1-yl phenyl sulfone and 2-chloroprop-2-en-1-yl methyl sulfone were determined by X-ray analysis.
- Nikonova,Kaliev,Borodina,Smirnov,Rozentsveig,Korchevin
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p. 1912 - 1917
(2020/01/31)
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- General [4 + 1] Cyclization Approach to Access 2,2-Disubstituted Tetrahydrofurans Enabled by Electrophilic Bifunctional Peroxides
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A general [4 + 1] cyclization reaction of carbonyl nucleophiles with 2-iodomethylallyl peroxides, which function as unique electrophilic oxygen synthons, for the synthesis of a broad range of 2,2-disubstituted tetrahydrofurans is achieved under operationally simple conditions. The unprecedented asymmetric version of such reaction is also realized via chiral auxiliary-assisted cyclization, thus providing a distinct approach to access chiral tetrahydrofurans with high diastereoselectivities. The new method can be applied to the synthesis of core structure of posaconazole drug.
- Gao, Min,Zhao, Yukun,Zhong, Chen,Liu, Shengshu,Liu, Pengkang,Yin, Qi,Hu, Lin
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supporting information
p. 5679 - 5684
(2019/08/01)
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- Switching of Sulfonylation Selectivity by Nature of Solvent and Temperature: The Reaction of β-Dicarbonyl Compounds with Sodium Sulfinates under the Action of Iron-Based Oxidants
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Selectivity of sulfonylation of β-keto esters with sodium sulfinates under the action of iron(III) salts as oxidants can be regulated by the type of solvent used and the reaction temperature. α-Sulfonyl β-keto esters are obtained when the process is conducted in THF/H2O solution at 40 °C. The change of the solvent to iPrOH/H2O and refluxing of a reaction mixture provides α-sulfonyl esters – the products of successive sulfonylation-deacylation. When β-diketones are applied as starting materials, only α-sulfonyl ketones are formed. The reaction pathway includes sulfonylation of dicabonyl compounds under the action of Fe(III) to form α-sulfonylated dicarbonyl compounds, which are then attacked by a solvent as the nucleophile, resulting in the products of successive sulfonylation-deacylation. Participation of the solvent in the reaction pathway determines the products structure.
- Mulina, Olga M.,Pirgach, Dmitry A.,Nikishin, Gennady I.,Terent'ev, Alexander O.
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p. 4179 - 4188
(2019/05/08)
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- A DEVELOPING AGENT PRECURSOR FOR LASER MARKABLE COMPOSITIONS
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The invention relates to novel laser markable compositions comprising developing agent precursors according to formula (I).
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Paragraph 0145
(2019/01/07)
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- Manganese(III)-Mediated and -Catalyzed Decarboxylative Hydroxysulfonylation of Arylpropiolic Acids with Sodium Sulfinates in Water
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With water as both solvent and reactant, a novel manganese(III)-mediated and -catalyzed synthesis of β-ketosulfones through decarboxylative hydroxysulfonylation reactions of arylpropiolic acids with sodium sulfinates is described. This protocol has the advantages of mild reaction conditions, short reaction time, easy to handle reagents, purification simplicity, and being environmentally benign, which demonstrate the practical utility of this methodology. (Figure presented.).
- Xiong, Yan-Shi,Weng, Jiang,Lu, Gui
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supporting information
p. 1611 - 1616
(2018/03/05)
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- Generation of 1,2-oxathiolium ions from (arysulfonyl)- and (arylsulfinyl)allenes in Br?nsted acids. NMR and DFT study of these cations and their reactions
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In strong Br?nsted acids (CF3SO3H, FSO3H, D2SO4), (arysulfonyl)allenes (ArSO2-CR1=C=CR2R3) and (arylsulfinyl)allenes (ArSO-CR1=C=CR2R3) undergo cyclization into the corresponding stable 1,2-oxathiolium ions, which were studied by means of NMR and DFT calculations. Quenching of solutions of these cations with low nucleophilic media, aqueous HCl, leads to their deprotonation with a stereoselective formation of (arysulfonyl)butadienes (for instance, ArSO2-CR1=C-C(Me)=CH2, for R2 = R3 = Me, yields of 87-98%). Reactions of (arysulfonyl)allenes in the system TfOH (0.1 equiv)-HFIP (hexafluoropropan-2-ol) followed by hydrolysis give rise to allyl alcohols (ArSO2-CR1=CH-C(OH)R2R3, yields of 78-99%). Reflux of solutions of (arysulfonyl)allenes in the presence of TfOH (1 equiv) in 1,2-dichlorobenzene leads to the cyclization into thiochromene 1,1-diox-ides in high yields. Under the action of TfOH or AlX3 (X = Cl, Br) followed by hydrolysis of reaction mixtures, (arylsulfinyl)allenes give allyl alcohols (ArSO2-CR1=CH-C(OH)R2R3). Plausible reaction mechanisms have been proposed for all studied reactions.
- Lozovskiy, Stanislav V.,Ivanov, Alexander Yu.,Khoroshilova, Olesya V.,Vasilyev, Aleksander V.
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supporting information
p. 2897 - 2906
(2018/12/13)
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- N-bromosuccinimide mediated decarboxylative sulfonylation of β-keto acids with sodium sulfinates toward β-keto sulfones: Evaluation of human carboxylesterase 1 activity
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A N-bromosuccinimide (NBS) mediated decarboxylative sulfonylation of β-keto acids with sodium sulfinates is developed. The transformation exhibits a broad substrate scope and good functional group tolerance. Preliminary mechanistic studies showed that this reaction is likely to proceed through a nucleophilic substitution of β-keto acid with sulfonyl bromide pathway. All synthesized β-keto sulfones were evaluated the inhibitory effect against human carboxylesterase 1 (CES1). This investigation offers an expedient strategy for efficient synthesis of β-keto sulfones that are widely present in biologically active natural products and pharmaceutical agents.
- Han, Fuzhong,Su, Bobo,Song, Peifang,Wang, Yaqiao,Jia, Lina,Xun, Shanshan,Hu, Minggang,Zou, Liwei
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p. 5908 - 5913
(2018/08/29)
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- Copper-catalyzed chemoselective cross-coupling reaction of thioamides and α-diazocarbonyl compounds: Synthesis of enaminones
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The development of operationally simple and cost-effective methods for C[sbnd]C bond formation reactions are highly important in pharmaceutical, agrochemical and material research. In this article we describe the first copper-catalyzed cross-coupling reaction of thioamides with acceptor/acceptor-substituted and acceptor-only substituted α-diazocarbonyl compounds to yield enaminones. The reaction shows broad substrate scope in terms of thioamides and diazocarbonyl compounds. Primary, secondary and tertiary thioamides all give enanminones when reacted with α-diazodiesters, α-diazoketoesters, α-diazodiketones, α-diazoketoamides, α-diazoesteramides, α-diazoketosulfones and α-diazomonoketones.
- Pal, Arpal,Koduri, Naga D.,Wang, Zhiguo,Quiroz, Erika Lopez,Chong, Alexandra,Vuong, Matthew,Rajagopal, Nisha,Nguyen, Michael,Roberts, Kenneth P.,Hussaini, Syed R.
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supporting information
p. 586 - 589
(2017/01/16)
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- Synthesis of β-Keto Sulfones by a Catalyst-Free Reaction of Aryldiazonium Tetrafluoroborates, Sulfur Dioxide, and Silyl Enol Ethers
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A green approach for the generation of β-keto sulfones through a reaction of aryldiazonium tetrafluoroborates and sulfur dioxide with silyl enol ether under catalyst- and additive-free conditions has been realized. This reaction proceeds efficiently at room temperature and goes to completion in half an hour. During the reaction process, aryldiazonium tetrafluoroborate is treated with DABCO?(SO2)2 (DABCO=1,4-diazabicyclo[2.2.2]octane) to provide a sulfonyl radical as the key intermediate, which then initiates the transformation. Oxidants or metal catalysts are avoided, and the presence of DABCO also plays an important role in the reaction.
- Liu, Tianshuo,Zheng, Danqing,Ding, Yechun,Fan, Xiaona,Wu, Jie
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supporting information
p. 465 - 469
(2017/02/23)
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- Preparation method of beta-ketosulfone
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The invention discloses a preparation method of beta-ketosulfone. The preparation method of the beta-ketosulfone comprises the steps of adding beta-ketonic acid, N-bromosuccinimide and sodium sulfinate into a reaction test tube, then adding water and sodium phosphate dodecahydrate, and heating to 20 to 25 DEG C for reacting for 12 to 24 hours; after finishing reaction, extracting with ethyl acetate for three times, drying an organic phase with anhydrous sodium sulfate, carrying out vacuum concentration to remove a solvent, and performing silica-gel column chromatography to finally obtain a corresponding product. The problems that during the preparation of the beta-ketosulfone, halohydrocarbon and a pre-functionalized substrate with high toxicity need to be used, and a toxic solvent is used are solved.
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Paragraph 0042; 0043
(2017/08/31)
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- A 1,3-diones substitution alkone method of synthesizing α-
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The invention discloses a method for synthesizing alpha-substituted ketone by using a 1,3-diketone compound, and belongs to the field of preparation of fine chemical engineering. The 1,3-diketone compound with an electron-withdrawing substituent group at 2-position is used as a substrate, an accelerant is added, and alpha-substituted ketone is synthesized by utilizing mixed solvent of tetrahydrofuran and water. An efficient and single method for synthesizing the alpha-substituted ketone, which is mild in condition, low in cost and suitable for large-scale production is provided.
- -
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Paragraph 0039; 0040; 0041; 0042; 0043
(2016/10/10)
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- Chemoselective one-pot synthesis of β-keto sulfones from ketones
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A practical method to synthesize substituted β-keto sulfones directly from ketones at room temperature has been developed. This method involves the nucleophilic addition of a base generated enolate to sulfonyl iodide. The reaction shows high chemoselectivity for the addition of a sulfonyl group to an α-carbon over a hydroxyl group. In addition, the given protocol provides good to excellent yields of β-keto sulfones under mild reaction conditions. Moreover, the regiochemical aspect of the protocol is also explored.
- Rawat, Vikas S.,Reddy, Perla L. M.,Sreedhar, Bojja
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p. 5165 - 5168
(2014/01/23)
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- Dual secondary amine/N-heterocyclic carbene catalysis in the asymmetric Michael/cross-benzoin cascade reaction of β-oxo sulfones with enals
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Polyfuncionalized cyclopentanones with three contiguous stereogenic centers were formed in good to excellent yields and stereoselectivities by utilizing a secondary amine/N-heterocyclic carbene catalytic system in the reaction of β-oxo sulfones with unsaturated aldehydes. In addition, the influence of the catalysts on the diastereoselectivity of the final product was studied by 1H NMR spectroscopy. The combination secondary amine/N-heterocyclic carbene turned out to be a good dual catalytic system for the reaction of β-oxo sulfones with enals leading to polyfunctionalized cyclopentanones in good to excellent yields and stereoselectivities. Further improvement of the enantiomeric excess is possible by crystallization. Direct observations by NMR spectroscopy revealed that the carbene catalyst alone is triggering the diastereoselectivity.
- Enders, Dieter,Grossmann, Andre,Huang, He,Raabe, Gerhard
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supporting information; experimental part
p. 4298 - 4301
(2011/09/16)
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- TiO2 nanoparticles and Preyssler-type heteropoly acid modified nano-sized TiO2: A facile and efficient catalyst for the selective oxidation of sulfides to sulfones and sulfoxides
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A new and efficient synthetic method has been developed for the selective conversion of sulfides into their corresponding sulfones and sulfoxides using H2O2 in the presence of neat or Preyssler-type heteropoly acid modified nano-sized TiO2 as catalyst, respectively. The reaction was performed at room temperature with quantitative yields. The catalyst is reusable without significant loss of activity for the next oxidation reaction.
- Rahimizadeh, Mohammad,Rajabzadeh, Ghadir,Khatami, Seyed-Mola,Eshghi, Hossein,Shiri, Ali
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scheme or table
p. 59 - 64
(2010/09/04)
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- An efficient fluorination of β-ketosulfones promoted by a room-temperature ionic liquid at ambient conditions under ultrasound irradiation using Selectfluor F-TEDA-BF4
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The fluorination reaction involving a β-ketosulfones by Selectfluor was efficiently promoted by the ionic liquid, [Hbim]BF4 (IL) as a reaction medium with methanol as co-solvent at room temperature under ultrasonic irradiation to afford the corresponding mono and difluoro-β-ketosulfones in excellent yields. The advantages of this method include among others the use of a recyclable, non-volatile ionic liquid, which promotes this protocol under room temperature without the requirement of any added catalyst under ultrasonic irradiation.
- Heravi, Mohammad Reza Poor
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body text
p. 1399 - 1402
(2011/10/08)
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- (Arylsulfonyl)acetones and -acetonitriles: New activated methylenic building blocks for synthesis of 1,2,3-triazoles
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β-Keto sulfones and b-nitrile sulfones were used as building blocks for 1,2,3-triazole synthesis in the Dimroth cyclization. It was shown, that sulfone reagents undergo base-catalyzed cyclization under mild conditions (at room temperature) to give 1,2,3-triazoles in moderate to excellent yields. This fact has confirmed the high nucleophilicity of sulfonylmethylenic compounds and allows new synthetic applications. Georg Thieme Verlag Stuttgart.
- Pokhodylo, Nazariy T.,Matiychuk, Vasyl S.,Obushak, Mykola D.
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scheme or table
p. 2321 - 2323
(2010/02/16)
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- A facile one-pot synthesis of β-keto sulfones from ketones under solvent-free conditions
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An easy solvent-free method is described for the conversion of ketones into β-keto sulfones in high yields that involves the in situ generation of α-tosyloxyketones, followed by nucleophilic substitution with sodium arene sulfinate in the presence of tetra-butylammonium bromide at room temperature. The salient features of this one-pot protocol are short reaction times, cleaner reaction profiles, and simple work-up that precludes the use of toxic solvents.
- Kumar, Dalip,Sundaree, Swapna,Rao,Varma, Rajender S.
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p. 4197 - 4199
(2007/10/03)
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- Facile polyethylene glycol (PEG-400) promoted synthesis of β-ketosulfones
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An efficient and convenient synthesis of β-ketosulfones is described. Reaction of an α-haloketone with sodium alkyl/aryl sulphinate yields the corresponding β-ketosulfone promoted by polyethylene glycol (PEG-400) as an efficient reaction medium.
- Suryakiran,Reddy, T. Srikanth,Ashalatha,Lakshman,Venkateswarlu
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p. 3853 - 3856
(2007/10/03)
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- New access to 1,3-diketones from aldehydes
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A simple and efficient methodology to introduce an 1,3-diketone motif from various aldehyde precursors in three steps with good overall yields is described using β-ketosulphone 7 as masked equivalent of acetone. A three-step sequence was studied leading i
- Fargeas, Valérie,Baalouch, Myriam,Metay, Estelle,Baffreau, Jer?me,Ménard, Delphine,Gosselin, Pascal,Bergé, Jean-Pascal,Barthomeuf, Chantal,Lebreton, Jacques
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p. 10359 - 10364
(2007/10/03)
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- Hypervalent iodine in synthesis. 66. One pot preparation of β-keto sulfones by reaction of ketones, [hydroxy(tosyloxy) iodo] benzene, and sodium sulfinates
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One pot reactions of ketones, [hydroxy(tosyloxy)iodo] benzene and sodium sulfinates lead to the formation of the corresponding β-keto sulfones under mild conditions and in good yield.
- Xie,Chen
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p. 3145 - 3149
(2007/10/03)
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- A facile phase-transfer catalysed synthesis of some β-ketosulphones
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Reaction of phenacyl chloride with sodium benzenesulphinate in refluxing alcohol for 10-12 hr results in the formation of phenylsulphonylacetophenone in about 50% yield. However, use of triethyibenzylammonium chloride as phase- transfer catalyst in acetonitrile medium at room temp. gives the product in over 90% yield in 30 min's, reaction time. Optimum conditions are described for the above reaction by changing the solvent, catalyst, temperature and the type of phase-transfer catalysis itself. Using the optimum conditions, several β-ketosulphones have been synthesised in a facile manner by changing the α-haloketone and sulphinate salts.
- Ramaiah,Dubey,Ramanatham,Grossert,Hooper
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p. 297 - 301
(2007/10/03)
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- Carbanion-Accelerated Claisen Rearrangements. 6. Preparative and Stereochemical Studies with Sulfonyl-Stabilized Anions
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The aliphatic Claisen rearrangement is markedly accelerated by an arylsulfonylmethide substituent at position 2.The generality of this anion variant has been extensively examined (31 allyl vinyl ethers) with regard to substitution, stereochemistry, and an
- Denmark, Scott E.,Harmata, Michael A.,White, Kathleen S.
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p. 8878 - 8891
(2007/10/02)
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- OXIDATION OF SULFIDES BY IODYLARENES IN THE PRESENCE OF VANADYL ACETONYLACETONATE AS A CATALYST
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Key words: Sulfide oxidation; sulfoxide; iodylarene; vanadyl acetylacetonate.Iodylbenzene is a poor oxidant of sulfur, but in the presence of vanadyl acetylacetonate, sulfides are converted into sulfoxides, sulfones and S-dealkylated products.To improve the selectivity and the yield of this reaction, different substituted iodylarenes are used.The N-(paraiodylphenyl) palmitoylamid is a promising oxidant for synthetic purposes.
- Barret, R.,Pautet, F.,Bordat, P.,Tinland, B.,Daudon, M.
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- HYDRATION OF 1- AND 3-ARYLSULFONYL-1-PROPYNES AND ARYLSULFONYLALLENES
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The reactions of isomeric 1- and 3-arylsulfonyl-1-propynes and arylsulfonylallenes with primary aromatic amines in organic solvent-water system lead to arylsulfonyl-2-propanones.Unstable addition products (enamines) are formed in the reaction and then undergo hydration and are transformed into the ketones.
- Mikhailova, V. N.,Bulat, A. D.,Yurevich, V. P.,Ezhova, L. A.
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p. 1756 - 1759
(2007/10/02)
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- Tetra-n-butylammonium Oxone. Oxidations under Anhydrous Conditions
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Tetra-n-butylammonium Oxone, readily prepared as a white solid from commercially available Oxone, performs oxidations in anhydrous methylene chloride.Under these conditions, sulfides are oxidized to sulfones in the presence of amines, ketones, esters, car
- Trost, Barry M.,Braslau, Rebecca
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p. 532 - 537
(2007/10/02)
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- Switching of the Direction of Enzyme-Mediated Oxidation and Reduction of Sulfur-Substituted 2-Propanols and 2-Propanones
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Incubation of 1-(phenylsulfenyl)-2-propanone with Corynebacterium equi IFO 3730 grown on hexadecane at pH 6.5 afforded the corresponding 1-substituted S propanols. 1-(Phenylsulfinyl)-2-propanone was also reduced by the microorganism, the product being aff
- Ohta, Hiromichi,Kato, Yasuo,Tsuchihashi, Gen-ichi
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p. 2735 - 2739
(2007/10/02)
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- Addition Reactions of (Phenylsulfonyl)propadiene with 1-Pyrrolidinyl Enamines of Cyclic Ketones: Syntheses and Reactions of 1,3-Dienes Possessing an Allyl Sulfone Moiety
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Addition reactions of (phenylsulfonyl)propadiene (1) with various 1-pyrrolidinyl enamines have been investigated.Allene 1 and enamines of cyclic ketones (2, 7-14) readily underwent the Michael-type addition reactions at -50 deg C to give the adducts 3, 15-20, and/or their isomers 4 and 21-26, which apparently arose by base-catalyzed isomerization of the former.These adducts were conveniently converted into the corresponding 1,3-dienes possessing allyl sulfone moiety (28, 38-45) through allyl acetates (27, 30-37) by base-promoted (n-BuLi, -50 deg C) 1,4-elimination of acetic acid to vinyl sulfones followed by deconjugation to allyl sulfones.The synthetic versatility of these dienes was revealed by the Diels-Alder reactions with dimethyl acetylenedicarboxylate (DMAD) and alkylation reactions via α-sulfonyl carbanions.
- Hayakawa, Kenji,Takewaki, Makoto,Fujimoto, Ichiro,Kanematsu, Ken
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p. 5100 - 5105
(2007/10/02)
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- THE PREPARATION, SPECTRAL PROPERTIES, STRUCTURES, AND BASE-INDUCED CLEAVAGE REACTIONS OF SOME α-HALO-β-KETOSULFONES
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The halogenation of β-ketosulfones such as α-methylsulfonylacetophenone (1) and benzenesulfonylacetone (10) can be effected with sulfuryl chloride or pyridinium bromide perbromide.Regiochemical control can be achieved by control of stoichiometry and/or the reaction conditions.Detailed 1H and 13C nmr, and mass spectra are recorded for a series of halogenated β-ketosulfones, together with structures by X-ray crystallography for 1, 2-chloro-2-methylsulfonyl-1-phenylethanone (2), chloromethyl methyl sulfone (4), and α-chloroacetophenone (21).Results from these studies are used to suggest a reason for the difficulty associated with substitution reactions of α-halosulfones.
- Grosset, Stuart J.,Dubey, Pramod K.,Gill, Glen H.,Cameron, Stanley T.,Gardner, Patrick A.
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p. 798 - 807
(2007/10/02)
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- A NEW PROCEDURE FOR OXIDATION OF SULFIDES TO SULFONES
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A series of variously substituted sulfones has been synthesized by oxidation of the corresponding sulfides with the hydrogen peroxide/selenium dioxide system.Very short reaction time, easy work-up and high yields make this new preparation of sulfones a recommendable method.
- Drabowicz, Jozef,Lyzwa, Piotr,Mikolajczyk, Marian
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p. 169 - 172
(2007/10/02)
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- Production of carbonyl compounds substituted in α-position
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Production of carbonyl compounds substituted in the α-position and having the formula: EQU1 wherein R1 is alkyl, aralkyl, phenyl, toluyl, naphthyl, alkoxy or amino; R2 is hydrogen EQU2 A is hydrogen, alkyl, halo or EQU3 R6 is hydrogen or methyl, and R11 is alkyl; wherein said compounds are formed by reacting a sulfur ylide having the formula: EQU4 wherein Y is the radical EQU5 and R9 and R10 are alkyl or phenyl, with a solution containing both an electrophilic agent A' that is converted into the radical A and a nucleophilic agent B' that is converted into the radical B. The resulting carbonyl compounds are useful as starting materials for the production of paper, textile, and leather auxiliaries, plant protection agents, alkyd resins, polyesters and polyamides.
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