- Dibenzothiophenesulfilimines: A Convenient Approach to Intermolecular Rhodium-Catalysed C?H Amidation
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A sulfilimine-based Group 9 transition-metal-catalysed C?H amidation procedure is reported. Dibenzothiophene-based sulfilimines were shown to constitute a class of novel amidation reagents which enable the transfer of a wide range of N-sulfonyl and N-acyl
- Antoni, Patrick W.,Mackenroth, Alexandra V.,Mulks, Florian F.,Rudolph, Matthias,Helmchen, Günter,Hashmi, A. Stephen K.
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supporting information
p. 8235 - 8238
(2020/06/17)
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- Copper-catalyzed imination of sulfoxides and sulfides
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Sulfoximines and sulfilimines have attracted considerable interest among organic chemists. The Cu(II)-catalyzed imination of sulfoxides and sulfides using various N-fluoro benzenesulfonamides was investigated in this study. The scope of the reaction was demonstrated by using several substituted sulfides and sulfoxides. The flow strategy for the preparation of NH-sulfoximines was also examined. By trapping nitrene intermediates through triphenylphosphine, we found that the reaction was conducted through a metal-nitrene intermediate mechanism.
- Liu, Yuanyuan,Wang, Hanying,Yang, Xianjin
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supporting information
p. 4697 - 4702
(2019/07/22)
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- The Stabilized Cation Pool Method: Metal- and Oxidant-Free Benzylic C-H/Aromatic C-H Cross-Coupling
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Electrochemical oxidation of toluene derivatives in the presence of a sulfilimine gave benzylaminosulfonium ions as stabilized benzyl cation pools, which reacted with subsequently added aromatic nucleophiles to give the corresponding cross-coupling produc
- Hayashi, Ryutaro,Shimizu, Akihiro,Yoshida, Jun-Ichi
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supporting information
p. 8400 - 8403
(2016/07/27)
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- Highly efficient sulfimidation of 1,3-dithianes by Cu(I) complexes
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A series of four Cu(I) complexes were tested for sulfimidation of 1,3-dithianes in the presence of [N-(p-tolysulfonyl)imino]phenyliodinane (PhI=NTs) as the nitrene-transfer agent. Cu(TMPhen)(PPh3)Br is an efficient catalyst with more than 90% yield of the
- Giribabu,Singh, Surya P.,Patil, Nandkumar M.,Kantam, M. Lakshmi,Gupte, Sunil P.,Chaudhari, Raghunath V.
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p. 619 - 625
(2008/04/12)
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- Heterogeneous catalytic sulfimidation using immobilized Cu(acac) 2
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The heterogeneous sulfimidation of various sulfides by microencapsulated copper(II) acetylacetonate, [MC-Cu(acac)2], and Cu(acac)2 immobilized in ionic liquids using [N-(p-tolylsulfonyl)imino]phenyliodinane (PhI=NTs) as nitrene donor
- Lakshmi Kantam,Kavita,Neeraja,Haritha,Chaudhuri,Dehury
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p. 641 - 645
(2007/10/03)
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- Synthesis of acyclic α- and β-silyl sulfimides
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Conversion of acyclic α- and β-silyl Sulfides by their treatment with sodium salts of N-chlorosulfonamides into the corresponding previously unknown sulfimides is described. The process is accompanied by a competing reaction resulting in the formation of α- or β-silyl sulfoxides. β-Silyl sulfamide (9b) undergoes thermolysis to generate trimethylvinylsilane. The Royal Society of Chemistry 2000.
- Suslova, Elena N.,Kirpichenko, Svetlana V.,Albanov, Aleksandr I.,Shainyan, Bagrat A.
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p. 3140 - 3142
(2007/10/03)
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- Hydrogen-Transfer Polymerization of Vinyl Monomers Derived from p-Tolylsulfonyl Isocyanate and Acrylamide Derivatives
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The hydrogen-transfer polymerization of N-acryloyl-N′-p-tolylsulfonylurea (1) prepared by the reaction of p-Molylsulfonyl isocyanate with acrylamide, was carried out at 80°C for 24 h in N,N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), acetonitrile (MeCN), and toluene containing N-phenyl-2-naphthylamine (1 mol%) as a radical inhibitor using t-BuOK or 1,3-diazabicyclo[5.4.0]undec-7-ene (DBU) (3 mol%) as an initiator. Polymers obtained by t-BuOK in polar solvents were composed of the hydrogen-transfer polymerization unit selectively, while those afforded by t-BuOK in less polar solvents or by DBU were composed of both the hydrogen-transfer and the vinyl polymerization units. Although Naciyloyl-N-methyl-N′-p-tolylsulfonylurea (2) prepared by the reaction of p-tolylsulfonyl isocyanate with N-methylacrylamide, gave low molecular-weight compounds (6-8) via the generation of the sulfonyl isocyanate, N-acryloyl-N′-methylN′-p-tolylsulfonylurea (3) underwent the selective hydrogen-transfer polymerization.
- Iwamura, Takeru,Tomita, Ikuyoshi,Suzuki, Masato,Endo, Takeshi
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p. 1137 - 1144
(2007/10/03)
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- Unconventional Regiospecific Syntheses of Aromatic Carbonamides and Thiocarbonamides by Means of Tin-Mediated Friedel-Crafts Reactions
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Friedel-Crafts reactions of stannylarenes 1 with tosyl isocyanate (TsNCO, 2) give N-tosylcarbonamides 3 via ipso substitution of the stannyl group.Thus, unconventionally substituted aromatic carbonamides can be obtained.The combination of the reaction of 1 and 2 with that of 1 and chlorosulfonyl isocyanate (14) allows one-pot syntheses of N-(arylsulfonyl)-substituted aromatic carbonamides with optional substitution patterns on both aromatic rings.The known ipso-specific substitutions of stannylarenes with 14 are extended to bi- and tricyclic arenes as well as to thiophenes 6 and 22.One stannyl group can serve as a leaving group for two aromatic systems, as shown with diaryldialkyltins 29.Also, stannylalkanes such as 27 react with 14 to afford alkylsulfonyl isocyanates and products of further reactions, such as 28.From the reactions of 1 with ethoxycarbonyl isocyanate (32), ortho- and meta-substituted aromatic thiocarbonamides 33 which are potential precursors for further syntheses, are accessible.The scope, limitations, and mechanism of these electrophilic substitutions are outlined.
- Arnswald, Martin,Neumann, Wilhelm P.
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p. 7022 - 7028
(2007/10/02)
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- Syntheses and Reactions of 1,7-Bis(tosyl) Trisulfur Tetranitride
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The syntheses and reactions of the new trisulfur tetranitride 6, an oligomeric analogue of polysulfur nitride, is reported.
- Lux, Rudolf,Kresze, Guenter
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p. 605 - 606
(2007/10/02)
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- Chemistry of Reactive Cations Derived from Sulfur Dioxide Analogues, XIII. - Preparation and Cycloaddition Reactions of Cationic Sulfur Diimides
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Two types of unsymmetrically substituted cationic sulfur diimides (1 and 2) have been synthestized.Diels-Alder reactions with 1 and 2 proceed regiospecifically in accordance with earlier hypotheses.
- Schwoebel, Alfred,Kresze, Guenter
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p. 453 - 461
(2007/10/02)
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- Mechanism of the Reaction of Dialkyl Sulphides with Bromamine T in Alkaline Medium
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Bromamine T (p-MeC6H4SO2NBr-K+) reacts readily with dialkyl sulphides (R2S) to yield sulphoxides (R2SO) and sulphimides (R2SNTs).The kinetics of the reaction were investigated in buffered alkaline water-methanol solutions.In rate-determining steps HOBr and p-MeC6H4SO2NHBr formed in equilibrium reactions convert dialkyl sulphides into bromosulphonium (R2SBr+) intermediates (ρ* -1.22 and 1.11, ρI -13.3 and -14.4, respectively.).Electrophilic additions of Br+ to sulphur atom are significantly hindered by the steric effect of S-alkyl groups (δ 0.713 and 0.765, ρs 0.766 and 0.792, respectively).Products are rapidly formed from bromosulphonium ions by nucleophilic displacement with OH- and p-MeC6H4SO2NH- nucleophiles.Product distribution depends on pH and the concentration of p-MeC6H4SO2NH2 but is not influenced markedly by S-alkyl groups in sulphides.Results are compared with those obtained earlier for chloramine T.
- Ruff, Ferenc,Kucsman Arpad
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p. 1075 - 1080
(2007/10/02)
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- Selectivity in the Electrophilic Addition of Carbenes and Nitrenes to Aliphatic Sulphides and to 4-t-Butylthian
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Photogenerated bisalkoxycarbonyl- and diacetyl-carbenes add exclusively equatorially to 4-t-butylthian and exhibit selectivity in competitive additions to mixtures of dimethyl- and di-isopropyl sulphides.By contrast ethoxy-carbonyl- and p-tolylsulphonyl-nitrene give equal proportions of axial and equatorial adducts with the thian, and show no selectivity in competitive reactions with dialkyl sulphides.The results in most or all cases appear to be determined by kinetic control.
- Appleton, David C.,Bull, David C.,Kenna, James Mc,Kenna, Jean M. Mc,Walley, Andrew R.
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p. 385 - 390
(2007/10/02)
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