- Dual Roles of Rongalite: Reductive Coupling Reaction to Construct Thiosulfonates Using Sulfonyl Hydrazides
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A tunable and practical transformation of structurally diverse sulfonyl hydrazides into thiosulfonates in the presence of Rongalite (NaHSO 2·CH 2O) was developed. Transition-metal-free conditions, operational simplicity, and readily available reagents are the striking features of this protocol. It is the first example for the synthesis of thiosulfonates using sulfonyl hydrazides with the assistance of reductant. Additionally, the mechanistic studies revealed that this transformation probably undergoes via a reducing-coupling pathway.
- Zhang, Guofu,Fan, Qiankun,Zhao, Yiyong,Wang, Huimin,Ding, Chengrong
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- Preparation method of symmetric disulfide bond-containing compound
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The method comprises the following steps: adding a raw material and an oxidant to a reaction bottle containing a solvent; reacting 23W - 85W under the irradiation of 12 - 24h energy-saving lamps; and purifying the reaction product to obtain symmetrical disulfide bond-containing compounds. The raw material is mercaptan or thiophenol. The oxidizing agent is trichlorobromomethane, and the solvent is tetrahydrofuran. The method has the advantages of simple operation, high yield (70 - 90%), wide applicability, cheap and easily available raw materials, and provides a better way for the synthesis and production of symmetrical disulfide bond-containing compounds.
- -
-
Paragraph 0020; 0054-0056
(2021/11/21)
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- Synthesis and biological evaluation of disulfides as anticancer agents with thioredoxin inhibition
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Altered redox homeostasis as a hallmark of cancer cells is exploited by cancer cells for growth and survival. The thioredoxin (Trx), an important regulator in maintaining the intracellular redox homeostasis, is cumulatively recognized as a promising target for the development of anticancer drugs. Herein, we synthesized 72 disulfides and evaluated their inhibition for Trx and antitumor activity. First, we established an efficient and fast method to screen Trx inhibitors by using the probe NBL-SS that was developed by our group to detect Trx function in living cells. After an initial screening of the Trx inhibitory activity of these compounds, 8 compounds showed significant inhibition activity against Trx. We then evaluated the cytotoxicity of these 8 disulfides, compounds 68 and 69 displayed high cytotoxicity to HeLa cells, but less sensitive to normal cell lines. Next, we performed kinetic studies of both two disulfides, 68 had faster inhibition of Trx than 69. Further studies revealed that 68 led to the accumulation of reactive oxygen species and eventually induced apoptosis of Hela cells via inhibiting Trx. The establishment of a method for screening Trx inhibitors and the discovery of 68 with remarkable Trx inhibition provide support for the development of anticancer candidates with Trx inhibition.
- Wei, Xiangxu,Zhong, Miao,Wang, Song,Li, Lexun,Song, Zi-Long,Zhang, Junmin,Xu, Jianqiang,Fang, Jianguo
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-
- Sequential C-H activation enabled expedient delivery of polyfunctional arenes
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Modular construction of polyfunctional arenes from abundant feedstocks stands as an unremitting pursue in synthetic chemistry, accelerating the discovery of drugs and materials. Herein, using the multiple C-H activation strategy with versatile imidate esters, the expedient delivery of molecular libraries of densely functionalized sulfur-containing arenes was achieved, which enabled the concise construction of biologically active molecules, such as Bipenamol.
- Cai, Xiaoqing,Chen, Qian,Chen, Xiaojian,Gao, Yang,Huo, Yanping,Li, Xianwei,Ouyang, Wensen,Rao, Jianhang,Wang, Jie
-
supporting information
p. 8075 - 8078
(2021/08/20)
-
- Diaryl disulfides and thiosulfonates as combretastatin A-4 analogues: Synthesis, cytotoxicity and antitubulin activity
-
Diaryl disulfides and diaryl thiosulfonates were synthesized with the two phenyl rings of all compounds bearing identical halide substituents. Because of structural similarity to the potent antimitotic natural product combretastatin A-4 (CA-4), the compounds were examined for inhibition of tubulin polymerization, and the thiosulfonates were more active than the disulfides. The nine thiosulfonates had IC50 values ranging from 1.2 to 9.1 μM, as compared with 1.3 μM obtained with CA-4. The compounds thus ranged from equipotent with CA-4 to 7-fold less active. The nine disulfides had IC50 values ranging from 1.2 to 5.1 μM, as compared with 0.54 μM obtained with CA-4. The compounds thus ranged from less than half as active as CA-4 to over 9-fold less active. The most active members of each group, 2 g and 3c, in the assembly assay were modeled into the colchicine site. Compound 3c had significant hydrophobic interactions with β-tubulin residues CYS 241 and ALA 250, and its thiosulfonate bridge made a hydrogen bond with β-tubulin residue ASN 258. Compound 2 g had hydrophobic interactions with β-tubulin residues ALA 250, CYS 241 and ALA 254, but there was no significant interaction of the disulfide bridge with tubulin.
- Bai, Ruoli,Barbosa, Euzébio Guimar?es,Beatriz, Adilson,Hamel, Ernest,Khodyuk, Rejane Gon?alves Diniz,Louren?o, Estela Mariana Guimar?es,de Lima, Dênis Pires,dos Santos, Edson dos Anjos
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-
- Palladium-Catalyzed Picolinamide-Directed Benzylic C(sp3)?H Chalcogenation with Diaryl Disulfides and Diphenyl Diselenide
-
The first palladium-catalyzed direct benzylic C(sp3)?H chalcogenation with diaryl disulfides and diphenyl diselenide has been established. The coupling reaction proceeds between the thioether radical and palladiumcycle intermediate. Picolinamide serves as an excellent directing group for the C?H activation of benzylic C(sp3)?H and can be easily removed. The current protocol exhibits a relatively broad substrate scope and high functional group compatibility. A mechanistic study indicates that palladium(IV) intermediate is probably formed during the course of the reaction. (Figure presented.).
- Wang, Kai,Hou, Jiahao,Zhang, Changjun,Cheng, Ke,Bai, Renren,Xie, Yuanyuan
-
supporting information
p. 2947 - 2952
(2020/06/17)
-
- T BuOK-triggered bond formation reactions
-
Recently, inexpensive and readily available tBuOK has seen widespread use in transition-metal-free reactions. Herein, we report the use of tBuOK for S-S, S-Se, NN and CN bond formations, which significantly extends the scope of tBuOK in chemical synthesis. Compared with traditional methods, we have realized mild and general methods for disulfide, azobenzenes imine etc. synthesis.
- Xu, Yulong,Shi, Xiaonan,Wu, Lipeng
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p. 24025 - 24029
(2019/08/13)
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- Utilizing 2-phenylpropanal as coupling partner for C-S bond formation via sequential thioarylation and decarbonylation process: A novel strategy for the synthesis of aryl alkyl sulfides
-
In this study, first direct access to aryl alkyl sulfides employing 2-phenylpropanal as coupling partner is reported. Diaryl disulfides react with this aldehyde in the presence of morpholine and produce the corresponding sulfide products in high yields. In another part, disulfides are in situ generated in the reaction mixture from aryl halides/CuI/Cyanodithioformate and coupled with 2-phenylpropanal to access aryl alkyl sulfides.
- Shaikhi Shahidzadeh, Elham,Nowrouzi, Najmeh,Abbasi, Mohammad
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-
- LDHA ACTIVITY INHIBITORS
-
The invention provides compounds of formula (I), stereoisomers and pharmaceutically acceptable salts thereof: (I) wherein A1 to A4, R1 and RP are as defined herein. Such compounds are suitable for use in the treatment or prevention of diseases or conditions which are mediated by the activation of lactate dehydrogenase A (LDHA), for example cancer.
- -
-
Page/Page column 42
(2018/12/13)
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- PIPERIDINE-DIONE DERIVATIVES FOR USE AS CONTRACEPTIVES
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The invention relates to a method of reducing sperm motility or of contraception in a subject, said method comprising the step of administering to said subject an effective amount of a compound of formula (I), a stereoisomer, tautomer, pharmaceutically ac
- -
-
Page/Page column 31; 32
(2018/12/13)
-
- LDHA ACTIVITY INHIBITORS
-
The invention provides compounds of formula (I), stereoisomers, tautomers, pharmaceutically acceptable salts and prodrugs thereof: (I) wherein A1 to A6 and R1 to R4 are as defined herein. Such compounds are suit
- -
-
Page/Page column 45-46
(2018/12/13)
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- Oxidative dimerization of thiols to disulfide using recyclable magnetic nanoparticles
-
Abstract: Dimerization of thiol groups to disulfide is an important transformation in chemical processes. In this study, magnetic ion exchanged Montmorillonite-k10 was synthesized and characterized using FTIR, X-ray diffraction and scanning electron microscope techniques. Then, the application of the synthesized catalyst as an efficient oxidizing agent was evaluated in oxidative dimerization of different thiols to corresponding disulfides under optimal reaction conditions. The reaction was easily performed with aromatic, aliphatic and heterocyclic thiols. The magnetic catalyst was easily recovered by applying an external magnet and, further, was reused in successive reactions. Graphical Abstract: [Figure not available: see fulltext.]
- Masnabadi, Nasrin,Ghasemi, Mohammad Hadi,Beyki, Mostafa Hossein,Sadeghinia, Mohammad
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p. 1609 - 1618
(2017/02/15)
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- Chemoselective synthesis of diaryl disulfides via a visible light-mediated coupling of arenediazonium tetrafluoroborates and CS2
-
A highly efficient and chemoselective method for the synthesis of diaryl disulfides is developed via a visible light-promoted coupling of readily accessible arenediazonium tetrafluoroborates and CS2. This practical and convenient protocol provides a direct pathway for the assembly of a series of disulfides in an environmentally friendly manner with good to excellent yields.
- Leng, Jing,Wang, Shi-Meng,Qin, Hua-Li
-
supporting information
p. 903 - 909
(2017/06/23)
-
- An efficient and convenient method for the preparation of disulfides from thiols using oxygen as oxidant catalyzed by tert-butyl nitrite
-
An efficient and convenient tert-butyl nitrite-catalyzed selective aerobic oxidation of thiols has been developed. Under the optimal reaction conditions, a number of thiol derivatives including aromatic thiols, heteroaromatic thiols and aliphatic thiols can be converted into their corresponding disulfides in good to excellent yields.
- Yi, Shan-Li,Li, Mei-Chao,Hu, Xin-Quan,Mo, Wei-Min,Shen, Zhen-Lu
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p. 1505 - 1508
(2016/09/23)
-
- Diacetoxyiodobenzene mediated oxidative transformation of thione to disulfides
-
We have developed an efficient oxidative transformation of thione to disulfides using diacetoxyiodobenzene (DIB) in acetonitrile at room temperature. This strategy is suited for oxidation of thiols to disulfide also. The present oxidation protocol is mild reaction condition, column free, and a new route for disulfide formation.
- Singh, Sarangthem Joychandra,Devi, Nepram Sushuma
-
supporting information
p. 5941 - 5943
(2016/12/07)
-
- Dithioates of Meldrum's acid, dimedone, and barbituric acid, novel sulfur transfer reagents for the one-pot copper-catalyzed conversion of aryl iodides into diaryl disulfides
-
We report herein the first application of CH-acid dithioates as sulfur transfer reagents. A new route for the synthesis of diaryldisulfides using the copper-catalyzed conversion of aryl iodides in the presence of Melderum's acid, dimedone or barbituric acid dithioates is discussed.
- Habibi, Azizollah,Baghersad, Mohammad Hadi,Bilabary, Mina,Valizadeh, Yousef
-
supporting information
p. 559 - 562
(2016/01/20)
-
- Cubic Ag2O nanoparticle incorporated mesoporous silica with large bottle-neck like mesopores for the aerobic oxidative synthesis of disulfide
-
Highly stable, environmentally benign cubic Ag2O nanoparticles dispersed on mesoporous silica with large bottle-neck like mesopores were synthesized and characterized by BET surface area analysis, HR TEM, EDX, FTIR and powder XRD studies. The Ag2O nanoparticles were homogeneously distributed having an average size of 20-40 nm. The activity of the catalyst was probed through an efficient aerobic chemoselective oxidation of thiols to disulfides in water under atmospheric oxygen as the cheapest oxidant. Alkyl, aryl and imine containing symmetrical disulfides can be easily obtained in high yields under mild reaction conditions with no over oxidized product. The efficiency of the catalyst was further demonstrated as the highly sensitive imine bond was well sustained under these mild reaction conditions. Moreover, unlike the other literature precedents, in this present work, single crystal structures of both simple symmetrical disulphide as well as imine containing disulphides are reported for the first time. The catalyst is very much water compatible and can be recycled and reused for at least five cycles. The standard leaching experiment proved that the reaction was heterogeneous with this recyclable catalyst.
- Das, Paramita,Ray, Suman,Bhaumik, Asim,Banerjee, Biplab,Mukhopadhyay, Chhanda
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p. 6323 - 6331
(2015/02/19)
-
- α-Arylchalcogenation of acetone with diaryl dichalcogenide via metal-free oxidative C(sp3)-H bond functionalization
-
Direct α-arylchalcogenation of acetone with diaryl dichalcogenides has been achieved by using a mixture of TBHP and DTBP oxidants at 120 °C without transition-metal catalyst via oxidative C(sp3)-H bond functionalization. The method exhibits good functional group tolerance and products were isolated in moderate to high yields.
- Yan, Guobing,Borah, Arun Jyoti,Wang, Lianggui,Pan, Zhangjin,Chen, Shuangshuang,Shen, Xuqian,Wu, Xiangmei
-
supporting information
p. 4305 - 4307
(2015/06/22)
-
- The Chan-Lam reaction of chalcogen elements leading to aryl chalcogenides
-
A copper-catalyzed chalcogenation of arylboronic acids with elemental sulfur or selenium is established, which provides diaryl disulfides or diaryl monoselenides in moderate to good yields with excellent selectivities, respectively. Moreover, after sequential reduction and coupling with aryl/alkyl iodides in one pot, unsymmetrical monosulfides were obtained in good yields.
- Yu, Jin-Tao,Guo, Huan,Yi, Yuanqiuqiang,Fei, Haiyang,Jiang, Yan
-
supporting information
p. 749 - 752
(2014/04/03)
-
- Palladium catalyzed aryl(alkyl)thiolation of unactivated arenes
-
A general palladium-catalyzed aryl(alkyl)thiolation of various substituted unactivated arenes is accomplished for the synthesis of diverse unsymmetrical diaryl(alkyl) sulfides in good yield employing electrophilic sulfur reagent 6 derived from succinimide. The developed strategy was coupled with intramolecular arylation of a C-H bond to afford dibenzothiphene derivatives, an important moiety in material science as organic semiconductors.
- Saravanan, Perumal,Anbarasan, Pazhamalai
-
supporting information
p. 848 - 851
(2014/03/21)
-
- Simple conversion of thiols to disulfides in EtOH under ambient aerobic conditions without using any catalyst or additive
-
EtOH was found to be an excellent medium for the aerobic S-S coupling reactions of various alkyl and aryl thiols. A series of useful disulfides RSSR have been synthesised in good to excellent yields without using any additional catalyst, oxidant or additive. Moreover, most products could be obtained by simply removing the solvent after completion of the reaction. Satisfactory results were obtained for both mg- and g-scale reactions.
- Wang, Hang,Huang, Guojun,Sun, Yang,Liu, Yunyun
-
-
- Efficient silver-catalyzed direct sulfenylation and selenylation of rich arenes
-
An efficient protocol for silver/copper-cocatalyzed direct sulfenylation and selenylation of arenes with aryl disulfides and diselenides has been developed. This strategy exhibits excellent functional group tolerance and high regioselectivity. Mono sulfenylation and selenylation products can be exclusively achieved. This reaction provides a simple and practical route to the preparation of aryl sulfides and selenides. This journal is
- Yan, Guobing,Borah, Arun Jyoti,Wang, Lianggui
-
supporting information
p. 9557 - 9561
(2015/02/19)
-
- (NH 4) 6Mo 7O 34·4H 2O as an efficient, selective, and reusable catalyst for the oxidation of thiols to disulfides using potassium bromate
-
Ammonium molybdate, (NH 4) 6Mo 7O 34·4H 2O, is found to be an efficient and selective catalyst for the oxidation of thiols to corresponding disulfides using potassium bromate in aqueous acetonitrile as the solvent. Among various solvents tested, CH3CN/H2O showed better results in terms of the reaction yield and rate. In the absence of (NH4)6Mo 7O24·4H2O, the oxidation reaction is not selective for the formation of disulfides. The catalyst can be easily recovered after completion of the reaction and reused without any significant loss of its activity. [Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfer, and Silicon and the Related Elements for the following free supplemental files: Additional text and figures.]
- Bayraq, Samad Shoghpour,Nikseresht, Ahmad,Khosravi, Iman
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supporting information
p. 1236 - 1243
(2013/09/23)
-
- Bio-based green solvent mediated disulfide synthesis via thiol couplings free of catalyst and additive
-
The bio-based green solvent ethyl lactate has been found to be a particularly efficient medium for oxidative coupling reactions of thiols yielding a broad array of disulfides. As a green solvent, ethyl lactate has shown an interesting promotion effect on the transformation by mediating corresponding reactions with high efficiency without using any catalyst or additive. The Royal Society of Chemistry 2013.
- Liu, Yunyun,Wang, Hang,Wang, Chunping,Wan, Jie-Ping,Wen, Chengping
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p. 21369 - 21372
(2013/11/06)
-
- A mild and efficient protocol for oxidation of thiols to disulfides in water
-
A novel vanadium polyoxometalate [(C7H7)(CH 3)3N]3[H3V10O 28].3H2O works as a useful oxidant for the oxidation of thiols to disulfldes in water under mild reaction conditions in an excellent yield.
- Dewan, Anindita,Bora, Utpal,Kakati, Dilip K.
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experimental part
p. 231 - 234
(2012/07/13)
-
- Base-free oxidation of thiols to disulfides using selenium ionic liquid
-
We present here the results on the use of 1-n-butyl-3-methylimidazolium methylselenite, [bmim][SeO2(OCH3)], in the synthesis of symmetrical disulfides starting from thiols. This efficient and improved method is general for aromatic, aliphatic, and functionalized thiols affording the disulfides in good to excellent yields after easy work up. The use of a microwave accelerates the reaction and the [bmim][SeO2(OCH 3)] was reused for further oxidation reactions.
- Thurow, Samuel,Pereira, Vanda A.,Martinez, Débora M.,Alves, Diego,Perin, Gelson,Jacob, Raquel G.,Lenard?o, Eder J.
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experimental part
p. 640 - 643
(2011/02/28)
-
- An efficient and convenient method for preparation of disulfides from thiols using air as oxidant catalyzed by Co-Salophen
-
Disulfides have been synthesized by oxidation of thiols using air as oxidant catalyzed by Co-Salophen with high yields, mild and neutral conditions, and easy procedures of the catalyst. The products were confirmed by 1H NMR and IR.
- Chai, Pin Ji,Li, Yong Shu,Tan, Cheng Xia
-
experimental part
p. 1403 - 1406
(2012/06/01)
-
- An efficient and selective oxidation of sulfides and thiols with silica-supported 1,1,3,3-tetramethylguanidine/Br2 complex
-
Silica-supported 1,1,3,3-tetramethylguanidine/Br2 complex is an efficient reagent for the selective oxidation of aliphatic and aromatic sulfides to the corresponding sulfoxides and the oxidative coupling of thiols to disulfides in aqueous solution at room temperature in a short reaction time.
- Shaabani, Ahmad,Farhangi, Elham,Rahmati, Abbas
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experimental part
p. 463 - 468
(2010/06/19)
-
- Metal-free air oxidation of thiols in recyclable ionic liquid: A simple and efficient method for the synthesis of disulfides
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An efficient procedure for the oxidative coupling of alkyl, aryl and heteroaryl thiols with atmospheric oxygen is reported. The methodology utilizes BMIM-BF4 as a recyclable solvent and does not require support materials or metal salts. Symmetric disulfides are obtained in excellent yields.
- Singh, Devender,Galetto, Fabio Z.,Soares, Letiere C.,Rodrigues, Oscar E. Dorneles,Braga, Antonio Luiz
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experimental part
p. 2661 - 2665
(2010/07/18)
-
- Study on the reactions of 3-bromo-4-ethoxy-1,1,1-trifluoro-3-buten-2-one with benzenethiols promoted by InCl3?4H2O
-
In the presence of InCl3?4H2O, the reaction of 3-bromo-4-ethoxy-1,1,1-trifluoro-3-buten-2-one 2 with a series of benzenethiols proceeds readily and gave both the addition-elimination product 3-bromo-1,1,1-trifluoro-4-thiophenyl-but-3-en-2-one and substitution product 1,1,1-trifluoro-3,4-bis-thiophenyl-but-3-en-2-one. The reactivity of benzenethiols is discussed in terms of their substituted group.
- Zhao, Jingwei,Song, Tao,Jiang, Huiling,Xu, Liangzhong,Zhu, Shizheng
-
experimental part
p. 1623 - 1629
(2011/07/07)
-
- CuCl-catalyzed cleavage of S-triphenylmethyl thioether: a new detritylation method for thio group
-
A new method for the deprotection of trityl thioethers using CuCl as the catalyst under ultrasonic conditions is described.
- Ma, Ming,Zhang, Xiu,Peng, Lingling,Wang, Jianbo
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p. 1095 - 1097
(2008/01/27)
-
- Clean and fast oxidative transformation of thiols to disulfides under solvent-free conditions
-
We present here a fast, solvent-free synthesis of symmetrical disulfides using solid supported catalyst (Al2O3/KF). The reaction was performed at room temperature, by gentle heating or under MW irradiation. This efficient and improved method is general for liquid thiols, affording the disulfides in good to excellent yields. The catalytic system can be re-used two times without previous treatment and with comparable activity.
- Lenard?o, Eder J.,Lara, Renata G.,Silva, Márcio S.,Jacob, Raquel G.,Perin, Gelson
-
p. 7668 - 7670
(2008/03/30)
-
- BIPHENYLOXYACETIC ACID DERIVATIVES FOR THE TREATMENT OF RESPIRATORY DISEASE
-
The invention relates to substituted phenoxyacetic acids as useful pharmaceutical compounds for treating respiratory disorders, pharmaceutical compositions containing them, and processes for their preparation.
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Page/Page column 43
(2008/06/13)
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- Oxidation of thiols to bisulfides using silica chloride as a heterogeneous catalyst
-
Silica chloride is used as a selective and effective heterogeneous catalyst for the rapid conversion of thiols to disulfides with quantitative yields in a very short period of time. Copyright
- Sathe, Manisha,Ghorpade, Ramarao,Kaushik, Mahabir Parshad
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p. 1048 - 1049
(2007/10/03)
-
- Potassium permanganate oxidation of organic compounds
-
It has been discovered that potassium permanganate is an effective heterogeneous oxidant, even without resorting to the use of a solid support, if acetonitrile is employed as the solvent. Primary benzylic and secondary alcohols are converted to the corresponding aldehydes and ketones, alkyl arenes are oxidized to the corresponding α-ketones in good yields using this procedure, and both alkyl and aryl sulfides are smoothly converted to the corresponding sulfones, also in excellent yields. When methylene chloride is used as the solvent, instead of acetonitile, the yields of aldehydes, ketones, α-ketones, and sulfones are reduced. However, the oxidation of thiols to disulfides proceeds satisfactorily when methylene chloride is the solvent.
- Shaabani, Ahmad,Tavasoli-Rad, Farahnaz,Lee, Donald G.
-
p. 571 - 580
(2007/10/03)
-
- Simple and selective oxidation of thiols to disulfides with dimethylsulfoxide catalyzed by dichlorodioxomolybdenum(VI)
-
Selective and quantitative conversion of thiols to disulfides was effected by dimethyl sulfoxide under mild conditions catalyzed by dichlorodioxomolybdenum(VI).
- Sanz, Roberto,Aguado, Rafael,Pedrosa, María R.,Arnáiz, Francisco J.
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p. 856 - 858
(2007/10/03)
-
- Hydrotalcite clay-catalysed air oxidation of thiols
-
Hydrotalcite is an efficient catalyst for air oxidation of a variety of aromatic, aliphatic and alicyclic thiols in hexane, affording the corresponding disulfides in excellent to quantitative yields under mild and neutral conditions.
- Hirano, Masao,Monobe, Hiroyuki,Yakabe, Sigetaka,Morimoto, Takashi
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p. 374 - 375
(2007/10/03)
-
- Simple Oxidation of Thiols with Sodium lodate under Solid-Solution Biphasic Conditions
-
A variety of aromatic, aliphatic, and alicyclic thiols were readily oxidised with a combination of sodium iodate and Chromatographic neutral alumina in hexane to afford the corresponding disulfides in excellent yields under mild and neutral conditions.
- Hirano, Masao,Yakabe, Sigetaka,Ando, Ken-Ichiro,Morimoto, Takashi
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p. 816 - 817
(2007/10/03)
-
- Alumina: An Efficient and Reusable Catalyst for the Oxidative Coupling of Thiols with DMSO
-
An inexpensive combination of common laboratory reagents, dimethyl sulfoxide (DMSO) and Chromatographic neutral alumina, gives an efficient, selective, and high-yielding oxidation of aromatic, aliphatic and alicyclic thiols to the corresponding disulfides in excellent yields under relatively mild conditions.
- Hirano, Masao,Yakabe, Sigetaka,Monobe, Hiroyuki,Morimoto, Takashi
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p. 472 - 473
(2007/10/03)
-
- Oxidation by Chemical Manganese Dioxide. Part 2.1 Simple and High-yielding Synthesis of Symmetrical Disulfides via the Oxidative Coupling of Thiols
-
Aromatic, aliphatic, and alicyclic thiols readily underwent oxidative coupling with chemical manganese dioxide in hexane to afford the corresponding disulfides in essentially quantitative yields under relatively mild conditions.
- Hirano, Masao,Yakabe, Sigetaka,Chikamori, Hideki,Clark, James H.,Morimoto, Takashi
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p. 310 - 311
(2007/10/03)
-
- 1-Benzyl-1-aza-4-azoniabicyclooctane periodate as new oxidant for oxidation of thiols and sulfides to the corresponding disulfides and sulfoxides under anhydrous conditions
-
1-Benzyl-1-aza-4-azoniabicyclooctane periodate (BAABCOP) 1, readily prepared as an orange solid from commercially available DABCO (1,4-diazobicyclooctane) performs oxidation in anhydrous conditions. Under these conditions, thiols are selectively oxidised to disulfides. Sulfides are also oxidised to the corresponding sulfoxides under these conditions.
- Hajipour, A. R.,Mahboubghah, N.
-
p. 1041 - 1043
(2007/10/03)
-
- Efficient, high yield oxidation of thiols and selenols to disulphides and diselenides
-
Thiols and selenols are smoothly oxidised in high yield to disulphides and diselenides by sodium perborate at room temperature.
- McKillop,Koyuncu,Krief,Dumont,Renier,Trabelsi
-
p. 5007 - 5010
(2007/10/02)
-
- The Crystal Structure of Bis(2-chlorophenyl) Disulfide
-
The crystal structure of bis(2-chloropentyl) disulfide has been determined and refined to a residual of 0.035 for 1573 observed reflections.Crystals are monoclinic, space group P21/a with Z4 in a cell of dimensions a 7.724(1), b 22.360(7), c 7.
- Mak, Thomas C. W.,Yip, Wai-Hing,Chan, Wing-Hong,Smith, Graham,Kennard, Colin H. L.
-
p. 1403 - 1406
(2007/10/02)
-
- PREPARATION AND SPECTRAL PROPERTIES OF SYMMETRICAL S-ARYL ARENESULFONOTHIOATES (THIOSULFONATES)
-
Arenesulfinyl chlorides (4-XC6H4S(O)Cl; X = H, CH3, F, Cl, Br) react with activated zerovalent zinc in benzene at 6 to 8 deg C to give symmetrical S-aryl arenesulfonothioates (thiosulfonates) in good to excellent yields. 2- and 3-substituted arenesulfinyl chlorides (X=Cl, CH3) give a mixture of products (disulfide, thiosulfinate, and/or thiosulfonate). 2,4,6-Triisopropylbenzenesulfinyl chloride reacts with zinc in 1,2-dimethoxyethane to give S-(2,4,6-triisopropylphenyl) 2,4,6-triisopropylbenzenesulfinothioate and bis(2,4,6-triisopropylphenyl) disulfide.Possible mechanisms for the reaction, the 1H and 13C NMR spectra and the chemical ionization and electron impact mass spectra of the thiosulfonates are discussed.The para carbon substituent chemical shifts (Cp-SCS) for the thiosulfonates and for symmetrical diaryl disulfides have been subjected to several dual substituent parameter (DSP) correlations. Key Words: S-aryl-arenesulfonothioates (thiosulfonates); arenesulfinyl chlorides; 1H and 13C NMR; mass spectrometry; substituent shift parameters.
- Freeman, Fillmore,Bartosik, Lisa G.,Bui, Nghe Van,Keindl, Monica C.,Nelson, Eric L.
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p. 375 - 386
(2007/10/02)
-
- Barium Manganate Oxidation in Organic Synthesis: Part II - A Simple Method for Conversion of Thiols to Disulphides
-
The use of barium manganate as a simple and efficient reagent for effecting the oxidation of mercaptans to disulfides is described.
- Srivastava, Ram Gopal,Venkataramani, Pudukkottai S.
-
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