- Isocyanide-Induced Esterification of Sulfinic Acids to Access Sulfinates
-
The isocyanide-induced esterification of sulfinic acids with alcohols or thiophenols access to sulfinates has been developed. Various primary, secondary, and tertiary alcohols could be compatible with the established protocols. Notably, such an isocyanide-induced synthetic strategy presented the advantages of simple operation, good functional group tolerance, and more than 40 examples up to 99% yields. (Figure presented.).
- Yang, Jianjing,Dong, Haozhe,Yan, Kelu,Song, Xiaodan,Yu, Jie,Wen, Jiangwei
-
supporting information
p. 5417 - 5421
(2021/09/29)
-
- Direct synthesis of sulfinic esters via ultrasound accelerated tandem reaction of thiols and alcohols with N-bromosuccinimide
-
The direct transformation of various thiols and simple alcohols with N-bromosuccinimide into sulfinic esters has been investigated by using different categories of base/acidic catalysts as well as co-solvents under varied reaction conditions. The reaction was found out to afford the sulfinic esters with high yields in the absence of catalysts, especially within the shorter time under the acceleration of ultrasonic irradiation than under the longer-lasting conventional stirring conditions.
- Nguyen, Lan-Anh Thi,Le, Tri-Nghia,Duong, Cong-Thang,Vo, Chi-Tam,Duus, Fritz,Luu, Thi Xuan Thi
-
p. 519 - 528
(2021/05/27)
-
- Unified Approach to Benzo[ d]thiazol-2-yl-Sulfonamides
-
In this paper, we report a unified approach to N-substituted and N,N-disubstituted benzothiazole (BT) sulfonamides. Our approach to BT-sulfonamides starts from simple commercially available building blocks (benzo[d]thiazole-2-thiol and primary and secondary amines) that are connected via (a) a S oxidation/S-N coupling approach, (b) a S-N coupling/S-oxidation sequence, or via (c) a S-oxidation/S-F bond formation/SuFEx approach. The labile N-H bond in N-monoalkylated BT-sulfonamides (pKa (BTSO2N(H)Bn) = 3.34 ± 0.05) further allowed us to develop a simple weak base-promoted N-alkylation method and a stereoselective microwave-promoted Fukuyama-Mitsunobu reaction. N-Alkyl-N-aryl BT-sulfonamides were accessed with the help of the Chan-Lam coupling reaction. Developed methods were further used in stereo and chemoselective transformations of podophyllotoxin and several amino alcohols.
- Zále?ák, Franti?ek,Ková?, Ond?ej,Lachetová, Eli?ka,?t'astná, Nikola,Pospí?il, Ji?í
-
supporting information
p. 11291 - 11309
(2021/09/07)
-
- NaHSO3-Mediated Direct Synthesis of Sulfinic Esters from Sulfonyl Hydrazides under Transition-Metal-Free Conditions
-
We have developed a protocol for the NaHSO3-promoted esterification of sulfonyl hydrazides with alcohols for the synthesis of sulfinic esters. Various sulfonyl hydrazides could be converted to the corresponding sulfinic esters in good to high yields. The merits of this protocol include mild transition-metal-free reaction conditions, an inexpensive and available reagent, and operational simplicity. Controlled experiments reveal that this transformation probably undergoes via a radical pathway. (Figure presented.).
- Zhang, Guofu,Fan, Qiankun,Wang, Huimin,Zhao, Yiyong,Ding, Chengrong
-
p. 833 - 837
(2020/12/07)
-
- A aryl sulfonic acid ester compound synthesis method (by machine translation)
-
The invention relates to medicine, in the field of organic chemical and fine chemical industry, and in particular relates to a simple, highly efficient method for preparing aryl sulfonic acid ester compound. The method is to four fluoro boric acid aryl diazonium salt, double-(sulfur dioxide) - 1, 4 - diazabicyclo [2.2.2] octane adduct (DABSO) and alcohol as the raw material, the copper salt catalyst, under the presence of an oxidant, nitrogen protection, 50 - 100 °C heating under the reaction conditions, it took 10 - 15 hours synthetic aryl sulfonate. The reaction through simple after treatment can be a high yield a series of aryl sulfonic acid ester compound. On the benzene ring with various substituted aryl four fluoroborates, ordinary primary alcohol, secondary alcohol can be utilized as a reaction substrate, to obtain the corresponding asia sulfonic acid ester. (by machine translation)
- -
-
Paragraph 0024; 0038; 0039
(2019/06/12)
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- Ni/NHC-catalyzed cross-coupling of methyl sulfinates and amines for direct access to sulfinamides
-
It was reported to develop a simple and convenient method for the Ni/NHC-catalyzed cross-coupling of methyl sulfinates and amines without an acid/base to afford secondary or tertiary sulfinamides in moderate to good yields. The method can provide the desired products with broad substrate scope, good chemoselectivity and good functional group compatibility. The presented approach may enrich the Ni/NHC catalyst system and promote the applications of methyl sulfinates in the organic sulfur chemistry.
- Li, Gang-Jian,Pan, You-Lu,Liu, Yan-Ling,Xu, Hai-Feng,Chen, Jian-Zhong
-
supporting information
(2019/10/28)
-
- Metal- And oxidant-free electrochemical synthesis of sulfinic esters from thiols and alcohols
-
An efficient and eco-friendly electrochemical synthesis of various sulfinic esters from thiols and alcohols via sequential S-H/S bond cleavage and double S-O bond formation under mild reaction conditions has been developed. Stoichiometric oxidants, metal catalysts, activating agents and even added bases were avoided in this method, and the only by-product generated from this reaction was dihydrogen gas which could serve as a green source of energy. Various functional groups are compatible with this green protocol which can be easily conducted on a gram-scale.
- Ai, Chongren,Shen, Haiwei,Song, Dingguo,Li, Yujin,Yi, Xiao,Wang, Ze,Ling, Fei,Zhong, Weihui
-
supporting information
p. 5528 - 5531
(2019/10/22)
-
- N-Trifluoromethylthiolated Sulfonimidamides and Sulfoximines: Anti-microbial, Anti-mycobacterial, and Cytotoxic Activity
-
Herein we demonstrate the expanded utility of a recently described N-trifluoromethylthiolation protocol to sulfonimidamide containing substances. The novel N-trifluoromethylthio sulfonimidamide derivatives thus obtained were evaluated for antibacterial activity against Mycobacterium tuberculosis (M. tb.) and Mycobacterium abscessus and Gram + Ve (Streptococcus aureus, Bacillus subtilis), and Gram - Ve (Escherichia coli, Pseudomonas aeruginosa) bacteria. Two compounds, 13 and 15 showed high antimycobacterial activity with MIC value of 4-8 μg/mL; i.e. comparable to WHO recommended first line antibiotic for TB infection ethambutol. The same compounds were also found to be cytotoxic in HepG2 cells (compound 13 IC50 = 15 μg/mL; compound 15 IC50 = 65 μg/mL). A structure activity relationship, using matched pair analysis, gave the unexpected conclusion that the trifluoromethylthio moiety was responsible for the cellular and bacterial toxicity. Given the increasing use of the trifluoromethylthio group in contemporary medicinal chemistry, this observation calls for considerations before implementation of the functionality in drug design.
- Thota, Niranjan,Makam, Parameshwar,Rajbongshi, Kamal K.,Nagiah, Savania,Abdul, Naeem Sheik,Chuturgoon, Anil A,Kaushik, Amit,Lamichhane, Gyanu,Somboro, Anou M.,Kruger, Hendrik G.,Govender, Thavendran,Naicker, Tricia,Arvidsson, Per I
-
supporting information
p. 1457 - 1461
(2019/10/11)
-
- A sustainable oxidative esterification of thiols with alcohols by a cobalt nanocatalyst supported on doped carbon
-
Here, we developed a new cobalt nanocatalyst supported on N-SiO2-doped activated carbon (Co/N-SiO2-AC), which exhibits excellent catalytic performance towards the oxidative esterification of (hetero)aryl and alkyl thiols with alcohols. A wide array of sulfinic esters were efficiently afforded in an exclusive chemoselective manner. The developed synthetic method proceeds with the merits of mild reaction conditions, broad substrate scope, operational simplicity, good functional group tolerance, earth-abundant and reusable cobalt catalysts, the utilization of renewable alcohols as the coupling partners and molecular O2 as the sole oxidant, which offers a practical method for sustainable synthesis of sulfinic esters.
- Zhou, Changjian,Tan, Zhenda,Jiang, Huanfeng,Zhang, Min
-
supporting information
p. 1992 - 1997
(2018/05/23)
-
- Facile aerobic photo-oxidative synthesis of sulfinic esters
-
A mild and efficient one-pot visible light-induced method has been developed for the synthesis of sulfinic esters. Sulfinic esters are important structural elements that are frequently found in pharmaceutical agents and biologically active natural products. The routine procedure in the drug discovery and development process to prepare and fully characterize sulfinic esters make them a drug candidate for biological evaluation.
- Singh, Pravin K.,Singh, Praveen P.,Srivastava, Vishal
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p. 383 - 387
(2019/03/14)
-
- Using sulfinamides as high oxidation state sulfur reagent for preparation of sulfenamides
-
Traditional preparation of sulfenamides require the use of low oxidation state of sulfur reagent such as RSCl, (RS)2 or RSH, which are toxic, odorous and difficult to deal with due to the harsh reaction conditions. Here high oxidation state of
- Ma, Long-jun,Li, Guang-xun,Huang, Jin,Zhu, Jin,Tang, Zhuo
-
supporting information
p. 1600 - 1603
(2018/03/28)
-
- Highly Chemoselective NH- and O-Transfer to Thiols Using Hypervalent Iodine Reagents: Synthesis of Sulfonimidates and Sulfonamides
-
Aryl thiols can be selectively converted to sulfonimidates or sulfonamides with three new S-X connections being made selectively in one pot. Using hypervalent iodine reagents in the presence of ammonium carbamate, NH- and O-groups are transferred under mild and practical conditions. Reducing the loading of ammonium carbamate changed the product distribution, converting the sulfonimidate to the sulfonamide. Studies into the possible intermediate species are presented, suggesting that multiple pathways may be possible via sulfinate esters, or related intermediates, with each species forming the same products.
- Tota, Arianna,St John-Campbell, Sahra,Briggs, Edward L.,Estévez, Gala Ogalla,Afonso, Michelle,Degennaro, Leonardo,Luisi, Renzo,Bull, James A.
-
supporting information
p. 2599 - 2602
(2018/05/22)
-
- Copper-Catalyzed Oxidative Reaction of β-Keto Sulfones with Alcohols via C?S Bond Cleavage: Reaction Development and Mechanism Study
-
A Cu-catalyzed cascade oxidative radical process of β-keto sulfones with alcohols has been achieved by using oxygen as an oxidant. In this reaction, β-keto sulfones were converted into sulfinate esters under the oxidative conditions via cleavage of C?S bond. Experimental and computational studies demonstrate that a new pathway is involved in this reaction, which proceeds through the formation of the key four-coordinated CuII intermediate, O?O bond homolysis induced C?S bond cleavage and Cu-catalyzed esterification to form the final products. This reaction provides a new strategy to sulfonate esters and enriches the research content of C?S bond cleavage and transformations.
- Du, Bingnan,Wang, Wenmin,Wang, Yang,Qi, Zhenghang,Tian, Jiaqi,Zhou, Jie,Wang, Xiaochen,Han, Jianlin,Ma, Jing,Pan, Yi
-
supporting information
p. 404 - 408
(2018/02/21)
-
- Non-expensive, open-flask and selective catalytic systems for the synthesis of sulfinate esters and thiosulfonates
-
Two simple and efficient methods for the synthesis of sulfinate esters and thiosulfonates from sodium salts of sulfinic acids are described. Different alcohols were converted into the corresponding sulfinate esters in good yields and purity in an open flask. By the adjustment of the reaction conditions thiosulfonates could also be obtained in a very short reaction time.
- Tranquilino, Arisson,Andrade, Silvia R.C.P.,da Silva, Ana Paula M.,Menezes, Paulo H.,Oliveira, Roberta A.
-
supporting information
p. 1265 - 1268
(2017/03/10)
-
- Copper-Catalyzed Aerobic Oxidative Reaction of Sulfonyl Hydrazides with Alcohols: An Easy Access to Sulfinates
-
A Cu-catalyzed aerobic oxidative reaction between sulfonyl hydrazides and alcohols has been developed. In this reaction, sulfonyl hydrazides act as the sulfinic acid precursors to react with alcohols, resulting in sulfinic esters with up to 72 % yield. This catalytic system tolerates a wide range of sulfonyl hydrazide substrates, and represents a new strategy for the transformation of readily available sulfonyl hydrazides.
- Du, Bingnan,Li, Zan,Qian, Ping,Han, Jianlin,Pan, Yi
-
supporting information
p. 478 - 481
(2016/03/08)
-
- Alkyl sulfinates: Formal nucleophiles for synthesizing TosMIC analogs
-
Alkyl sulfinates function as formal nucleophiles in Mannich-type reactions to give sulfonyl formamides, which are readily dehydrated to the corresponding sulfonylmethyl isonitriles. The efficient, two-step synthesis provides a general route to sulfonylmethyl isonitriles from readily available methyl sulfinates or thiols. Mechanistic analysis reveals that the unusual nucleophlicity of the alkyl sulfinates arises from the in situ release of sulfinic acids.
- Lujan-Montelongo, J. Armando,Estevez, Angel Ojeda,Fleming, Fraser F.
-
supporting information
p. 1602 - 1605
(2015/03/04)
-
- COMPOSITION, SYNTHESIS, AND USE OF NEW ARYLSULFONYL ISONITRILES
-
This invention relates to novel isonitriles, including arylsulfonyl isonitriles, and methods for their synthesis. The isonitriles include a conjugated ring system. The structure is designed with the flexibility to have multiple substitution patterns. The isonitriles may be used in applications including, but not limited to, pharmaceutical compositions.
- -
-
Paragraph 0134-0136
(2015/09/23)
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- Tert-Butyl Sulfoxide as a Starting Point for the Synthesis of Sulfinyl Containing Compounds
-
Sulfoxides bearing a tert-butyl group can be activated using N-bromosuccinimide (NBS) under acidic conditions and then subsequently treated with a variety of nitrogen, carbon, or oxygen nucleophiles to afford a wide range of the corresponding sulfinic acid amides, new sulfoxides, and sulfinic acid esters.
- Wei, Juhong,Sun, Zhihua
-
supporting information
p. 5396 - 5399
(2015/11/18)
-
- Catalytic oxidation of alcohols and sulfides with hydrogen peroxide using isoindoline and phthalazine-based diiron complexes
-
A series of diiron(III) complexes of 1,3-bis(2′-arylimino) isoindoline, [(Fe(L)Cl)2O] and 1,4-di-(2′-aryl) aminophthalazine, [Fe2(μ-OMe)2(H2L)Cl 4], including new structurally characterized ligands, 1,4-di-(4′-methyl-2′-thiazolyl)aminophthalazine and 1,4-di-(2′-benzthiazolyl)-aminophthalazine, have been characterized, and used as catalysts for the oxidation of para-substituted phenyl methyl sulfides and benzyl alcohols. Hammett correlations and kinetic isotope effect experiments support the involvement of electrophilic metal-based oxidants. In case of [(Fe(L1,2)Cl)2O] catalysts, direct correlation has been found between the oxidative and catalase-like activity.
- Szávuly, Miklós,Szilvási, Szilvió D.,Csonka, Róbert,Klesitz, Dániel,Speier, Gábor,Giorgi, Michel,Kaizer, József
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p. 317 - 324
(2014/08/05)
-
- One-step synthesis of racemic α-amino acids from aldehydes, amine components, and gaseous CO2 by the aid of a bismetal reagent
-
α-Amino acids are essential resources for human life and are highly useful as building blocks for organic synthesis. The core framework of an α-amino acid can be divided into three basic components: an aldehyde, an amine, and carbon dioxide (CO2). We report herein that a one-step synthesis of α-amino acids has been successfully achieved from these three basic and inexpensive chemicals with a single operation, in which the mixture of an aldehyde, a sulfonamide, and gaseous CO2 was heated at 100 °C in the presence of Bu3Sn-SnBu3 and CsF. In this one-pot sequential protocol, two important intermediates (imine and α-amino stannane) are involved and the stannyl anion generated in situ plays a crucial role, particularly for the efficient stannylation of the imine in the presence of proton sources and for promoting retrostannylation of the undesired α-alkoxy stannane owing to its high stability and tolerance of the presence of proton sources. This methodology enabled the synthesis of a wide range of racemic arylglycine derivatives in high yields. Go retro! α-Amino acids are essential resources for human life and are highly useful as building blocks for organic synthesis. The core framework of an α-amino acid is retrosynthesized to an aldehyde, an amine, and carbon dioxide. A one-step synthesis of α-amin Copyright
- Mita, Tsuyoshi,Higuchi, Yuki,Sato, Yoshihiro
-
p. 1123 - 1128
(2013/02/23)
-
- Synthesis and arylation of unprotected sulfonimidamides
-
Herein we evaluate different methodologies for the synthesis of unprotected sulfonimidamides. Three different procedures that allow orthogonal deprotection of the imine nitrogen under acidic, nucleophilic, and basic conditions were established. Moreover,
- Funes Maldonado, Matías,Sehgelmeble, Fernando,Bjarnemark, Fanny,Svensson, Mats,?hman, Jens,Arvidsson, Per I.
-
experimental part
p. 7456 - 7462
(2012/09/22)
-
- Methyl sulfinates as electrophiles in friedel-crafts reactions. Synthesis of aryl sulfoxides
-
The Friedel-Crafts reaction of methyl alkyl- and arylsulfinates with aromatic systems, activated by one or more electron-donating substituents (OH, OMe, NHR, NR2), provides alkyl aryl and diaryl sulfoxides under mild conditions and in moderate to good yields. The very high regioselectivity usually observed in these sulfinylation reactions is rationalized on the basis of a Wheland intermediate having a trigonal bypyramidal structure in which steric and electronic interactions are significant factors strongly destabilizing the attack to the ortho positions.
- Yuste, Francisco,Hernandez Linares, Angelica,Mastranzo, Virginia M.,Ortiz, Benjamin,Sanchez-Obregon, Ruben,Fraile, Alberto,Garcia Ruano, Jose Luis
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scheme or table
p. 4635 - 4644
(2011/07/29)
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- The synthesis of sulfinylphthalimides and their reactions with some nucleophiles in dioxane
-
In this study, some N-(p-substituted-arylsulfinyl)phthalimides (1a-1e) were synthesized. The synthesized compounds were examined with respect to their substitution reactions with sodium ethoxide, sodium methoxide, methylamine, and t-butylamine in dioxane.
- Bozkurt, Yasemin Soydas,Kutuk, Halil
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p. 2250 - 2257
(2012/03/27)
-
- Discovery of 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride as a deoxofluorinating agent with high thermal stability as well as unusual resistance to aqueous hydrolysis, and its diverse fluorination capabilities including deoxofluoro-arylsulfinylation with high stereoselectivity
-
Versatile, safe, shelf-stable, and easy-to-handle fluorinating agents are strongly desired in both academic and industrial arenas, since fluorinated compounds have attracted considerable interest in many areas, such as drug discovery, due to the unique effects of fluorine atoms when incorporated into molecules. This article describes the synthesis, properties, and reactivity of many substituted and thermally stable phenylsulfur trifluorides, in particular, 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride (Fluolead, 1k), as a crystalline solid having surprisingly high stability on contact with water and superior utility as a deoxofluorinating agent compared to current reagents, such as DAST and its analogues. The roles of substiuents on 1k in thermal and hydrolytic stability, fluorination reactivity, and the high-yield fluorination mechanism it undergoes have been clarified. In addition to fluorinations of alcohols, aldehydes, and enolizable ketones, 1k smoothly converts non-enolizable carbonyls to CF2 groups, and carboxylic groups to CF3 groups, in high yields. 1k also converts C(=S) and CH3SC(=S)O groups to CF2 and CF3O groups, respectively, in high yields. In addition, 1k effects highly stereoselective deoxofluoro-arylsulfinylation of diols and amino alcohols to give fluoroalkyl arylsulfinates and arylsulfinamides, with complete inversion of configuration at fluorine and the simultaneous, selective formation of one conformational isomer at the sulfoxide sulfur atom. Considering the unique and diverse properties, relative safety, and ease of handling of 1k in addition to its convenient synthesis, it is expected to find considerable use as a novel fluorinating agent in both academic and industrial arenas.
- Umemoto, Teruo,Singh, Rajendra P.,Xu, Yong,Saito, Norimichi
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supporting information; experimental part
p. 18199 - 18205
(2011/03/18)
-
- An efficient and novel method for the synthesis of sulfinate esters under solvent-free conditions
-
The present letter describes a reliable one-stage process for the preparation of sulfinate esters from the corresponding sulfinic acid and alcohols in the presence of N,N′-dicyclohexylcarbodiimide (DCC) under solvent-free conditions.
- Hajipour, Abdol R.,Falahati, Ali R.,Ruoho, Arnold E.
-
p. 2717 - 2719
(2007/10/03)
-
- METHOD FOR PRODUCING SULFINIC ACID ESTER COMPOUND
-
PROBLEM TO BE SOLVED: To provide a method for producing a sulfinic acid ester compound without using a disulfide compound being a malodorous substance. SOLUTION: The method for producing the sulfinic acid ester compound represented by formula (4) (Ar is a
- -
-
Page/Page column 6-7
(2008/06/13)
-
- Anodic oxidation of chiral sulfinylamines: A new route to highly diastereoselective α-alkylation of piperidine
-
The anodic oxidation of some chiral non-racemic N-arylsulfinyl piperidines was investigated and for the first time α methoxylated sulfinyl piperidines were obtained. The so-formed compounds are equivalent of chiral N-sulfinyliminiums and used as new inter
- Turcaud, Serge,Martens, Thierry,Sierecki, Emma,Pérard-Viret, Jo?lle,Royer, Jacques
-
p. 5131 - 5134
(2007/10/03)
-
- Hammett Correlations in the Photosensitized Oxidation of 4-Substituted Thioanisoles
-
Singlet oxygen is quenched by a series of 4-substituted thioanisoles (methoxy to nitro), with rate constant kt = 7 × 104 to 7 × 106 M-1 s-1, close to the value observed for the myoglobin-catalyzed sulfoxidation of the same sulfides. Correlations with σ (ρ = -1.97) and with Eox (slope -3.9 V-1) are evidence for an electrophilic mechanism. In methanol sulfoxides are formed (85%) via an intermediate quenched by diphenyl sulfoxide; competing minor paths lead to arylthiols, arylsulfenic acid, and aryl sulfoxides. In aprotic solvents, the sulfoxidation is quite sluggish, but carboxylic acids (mostly ≤0.1 M) enhance the rate by a factor of > 100. The protonated persulfoxide is formed in this case and acts as an electrophile with sulfides, again with a rate constant correlating with σ (ρ = -1.78).
- Bonesi, Sergio M.,Fagnoni, Maurizio,Albini, Angelo
-
p. 928 - 935
(2007/10/03)
-
- Oxidation of thioanisole by hydrogen peroxide: Activation by nitrites
-
The oxidation of thioanisole (PhSMe) by H2O2 is activated by acetonitrile (MeCN) and propionitrile (EtCN) and involves the formation of a transient peroxyimidate, 1, by reaction of HO2 - and RCN, and 1 can be rapidly trapped by PhSMe. The rate of oxidation of PhSMe is then independent of the concentrations of PhSMe and of H2O2, but varies linearly with [HO2 -] and [RCN]. In very dilute PhSMe it and H2O2 compete in reacting with 1, and the rate then depends on [PhSMe]. The initial reaction gives PhSOMe, and subsequent formation of PhSO2Me is slow. The rates of oxidation are slightly higher than that expected from the MeCN-activated decomposition of H2O2, which involves a second molecule of H2O2 in conversion of the peroxyimidate into amide and oxygen. Copyright
- Gillitt, Nicholas D.,Domingos, Josiel,Bunton, Clifford A.
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p. 603 - 607
(2007/10/03)
-
- Synthesis of halfsandwich ruthenium complexes of sulfinic acid esters [1]
-
A series of halfsandwich ruthenium sulfinato complexes [CpRu(PR′3)2(SO2R)] (R = Me, CH2Ph, C2H4Ph, Ph, 4-C6H4Me; PR′3 = PMe3, 1/2 dppm) with various electronic and steric environments around the ruthenium centre, have been prepared by insertion of SO2 into a ruthenium carbon bond, by a direct ligand exchange reaction, or by oxidation of thiolato complexes with 3-chloroperoxybenzoic acid. The chiral complexes [CpRu(CO)(PPh3)(SO2R)] (R = Me, CH2Ph, Ph) were obtained similarly by oxidation of the corresponding thiolates with magnesium monoperoxyphthalate. Alkylation of the sulfinato complexes with oxonium salts [R″3O]X (R″ = Me, Et; X = BF4, PF6) gave ruthenium complexes of sulfinic acid esters, [CpRu(L)(L′)(S(O)(OR″)R)]X in high yields and, for the chiral complexes, up to 82% de. The esters may be detached from the metal by ligand exchange with acetonitrile. Stronger nucleophiles such as I- or SMe- dealkylate the coordinated sulfinic acid esters.
- Schenk, Wolfdieter A.,Kuhnert, Nikolai
-
p. 527 - 535
(2007/10/03)
-
- Degradation of the petroleum component's monomethylbenzothiophenes on exposure to light
-
The photochemical degradation of monomethylated benzo[b]thiophenes in aqueous solution was studied to elucidate the fate of crude oil components after an oil spill. One principal reaction pathway involves oxidation of the methyl group(s) to the carboxylic
- Bobinger, Stefan,Andersson, Jan T.
-
p. 2569 - 2579
(2007/10/03)
-
- Hypervalent iodine in synthesis. XXIV: A facile method for the preparation of arylsulfinic esters: Oxidation of disulfides or thiophenols by phenyliodine(III) bis(trifluoroacetate) in the presence of alcohols
-
Arylsulfinic esters were prepared by the oxidation of diaryl disulfides or thiophenols with phenyliodine(III) bis(trifluoroacetate) in the presence of alcohols.
- Xia,Chen
-
p. 1321 - 1326
(2007/10/03)
-
- Sulfinate esters from methoxymethyl sulfides
-
Several benzene (or phenylmethane) sulfinate esters were synthesized in 53-98% yields from the corresponding methoxymethyl (MOM) sulfides employing NBS as oxidant.
- Ko,Koo,Kim,Kim
-
p. 2871 - 2876
(2007/10/02)
-
- Unsaturation of ketones, nitriles and lactams with methyl phenylsulfinate
-
An improved synthesis of methyl phenylsulfinate 2 by treatment of diphenyl disulfide with bromine in the presence of methanol has been developed. Use of this reagent in the preparation of α,β-unsaturated ketones, nitriles and lactams is described.
- Resek, James E.,Meyers
-
p. 7051 - 7054
(2007/10/02)
-
- NMR of Terminal Oxygen, 6 - 17O NMR of the S-O 'Double Bond': Derivatives of Arylsulphinic and Arylsulphonic Acids
-
The 17O NMR spectra of terminal oxygen atoms in esters, anions and amides of substituted arenesulphinic acids and in esters and amides of substituted arenesulphonic acids were measured.The signals of the terminal O appear close to those of the bridge O.Co
- Dahn, Hans,Toan, Vien Van,Ung-Truong, My-Ngoc
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p. 897 - 903
(2007/10/02)
-
- ORGANOSULPHUR COMPOUNDS XLVII ALKYLATION OF SULPHINIC ACIDS BY O-ALKYLISOUREAS: O-VERSUS S-REACTIVITY AND ASYMMETRIC SYNTHESIS OF ALKYL SULPHINATES
-
The reaction of O-alkylisoureas with sulphinic acids was found to produce the corresponding sulphones and sulphinates, the latter being predominantly formed.The sulphinate to sulphone ratio is strongly influenced by the kind of alkyl groups in the O-alkylisourea and appeared to be also dependent on the solvent used.A few optically active sulphinates (e.e. up to 8.1percent) were prepared in the reaction between benzenesulphinic acid and a series of O-alkylisoureas bearing optically active substituents at the nitrogen atom.A possible reaction mechanism is discussed.
- Kielbasinski, Piotr,Zurawinski, Remigiusz,Drabowitz, Jozef,Mikolajczyk, Marian
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p. 6687 - 6692
(2007/10/02)
-
- Novel Base-induced Reactions of Substituted (1,2-Benzisoxazol-3-yl)acetates
-
The reactions of substituted (1,2-benzisoxazol-3-yl)acetates with strong bases are described.The esters (1) and (2) having electron-donating and dialkylamino substituents undergo novel ring transformations on treatment with NaH, ButOK, or MeONa
- Ueda, Shozo,Naruto, Shunsuke,Yoshida, Toyokichi,Sawayama, Tadahiro,Uno, Hitoshi
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p. 1013 - 1022
(2007/10/02)
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- 'One-Pot' Synthesis of Sulphinic Esters from Disulphides
-
Alkane- and arenesulphinic esters can conveniently be prepared from disulphides and alcohols using N-bromosuccinimide or a combination of 3-chloroperoxybenzoic acid and N-bromosuccinimide.
- Brownbridge, Peter,Jowett, Ian C.
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p. 252 - 254
(2007/10/02)
-
- A Novel Electro-oxidative Methoxylation of Cyanomethyl Sulphides
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Electrolysis of alkylthioacetonitriles (1) in the presence of toluene-p-sulphonic acid as an electrolyte in methanol readily affords synthetically useful α-methoxylated sulphides (2) possibly by way of a Pummerer-type intermediate.
- Kimura, Makoto,Koie, Kazuhiro,Matsubara, Shinichi,Sawaki, Yasuhiko,Iwamura, Hiizu
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p. 122 - 123
(2007/10/02)
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- A CONVENIENT PREPARATION OF SULFINIC ACIDS BY THE REACTION OF 2-SULFONYLPYRIDINES AND THEIR N-OXIDES WITH NUCLEOPHILES
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Ipso-substitution reaction of 2-sulfonylpyridines and their N-oxides with alkoxide or thiolate anion afforded the sodium salts of sulfinic acids together with the corresponding substitution product in high yields.This procedure becomes a convenient and versatile method for preparation of various sulfinic acids.
- Furukawa, Naomichi,Tsuruoka, Masayuki,Fujihara, Hisashi
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p. 3019 - 3022
(2007/10/02)
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- The reactions of some α-halo-β-ketosulfones with hard and soft nucleophiles. A preparation of sulfinate esters
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The α-halo-β-ketosulfonyl functionality was attacked by ethanethiolate at the halogen which, in the presence of a proton source, usually resulted in reduction to the β-ketosulfone.A range of other soft nucleophiles did not react, whereas hard nucleophiles invariably attacked at the carbonyl, with subsequent cleavage to α-halosulfones.Ambident arylsulfinate anions usually attacked at halogen to form the sulfonyl halide, which reacted with excess sulfinate to give an intermediate that is readily attacked by alcohols.This reaction resulted in the formation of alkyl arylsulfinate esters in reasonable yields.The same reaction occurred when sulfonyl chlorides were reacted with sulfinate salts and it was rationalized by using HSAB principles.Spectral properties of some sulfinate esters are presented.
- Grossert, J. Stuart,Dubey, Pramod K.,Elwood, Tom
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p. 1263 - 1267
(2007/10/02)
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- A CONVENIENT PREPARATION OF SULPHINIC ESTERS FROM SULPHINYL CHLORIDES AND CHLOROSULPHITES USING HEXAMETHYLDISILOXANE AS CHLORIDE ANION ACCEPTOR
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Sulphinic esters can be obtained in high yields by the reaction of sulphinyl chlorides with chlorosulphites in the presence of hexamethyldisiloxane and catalytic amount of dimethyl sulphoxide.
- Drabowicz, Jozef
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p. 1753 - 1754
(2007/10/02)
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- Physical Properties and Various Reactions of Thionitrites and Related Substances
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Several new sulfenyl or sulfonyl derivatives, thionitrates (RSNO2), sulfonyl nitrites (RSO2NO), were successfully isolated by treating corresponding thiols and sulfinic acids with dinitrogen tetraoxide (N2O4).Spectroscopic data of both stable and many rather unstable compounds were determined and compared with those of corresponding alkyl nitrites (RONO) or alkyl nitrates (RONO2).Chemical reactivities of these uncommon, novel S-nitroso and S-nitro compounds were investigated.
- Oae, Shigeru,Shinhama, Koichi,Fujimori, Ken,Kim, Yong Hae
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p. 775 - 784
(2007/10/02)
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