- Synthesis, Crystal Structure and Electronic Properties of a 2Fe-2S Complex with a Bulky Thiolato Ligand, 2
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The complex 2 (tmbt = 2,4,6-trimethylbenzenethiolate) was synthesised and its molecular structure determined.The crystal system is monoclinic with a = 15.241(6), b = 16.174(5), c = 16.768(6) Angstroem, β = 135.84(2) deg and Z = 2, in s
- Ueyama, Norikazu,Ueno, Satoru,Sugawara, Takashi,Tatsumi, Kazuyuki,Nakamura, Akira,Yasuoka, Noritake
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- Nonheme iron-thiolate complexes as structural models of sulfoxide synthase active sites
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Two mononuclear iron(ii)-thiolate complexes have been prepared that represent structural models of the nonheme iron enzymes EgtB and OvoA, which catalyze the O2-dependent formation of carbon-sulfur bonds in the biosynthesis of thiohistidine compounds. The series of Fe(ii) complexes reported here feature tripodal N4 chelates (LA and LB) that contain both pyridyl and imidazolyl donors (LA = (1H-imidazol-4-yl)-N,N-bis((pyridin-2-yl)methyl)methanamine; LB = N,N-bis((1-methylimidazol-2-yl)methyl)-2-pyridylmethylamine). Further coordination with monodentate aromatic or aliphatic thiolate ligands yielded the five-coordinate, high-spin Fe(ii) complexes [FeII(LA)(SMes)]BPh4 (1) and [FeII(LB)(SCy)]BPh4 (2), where SMes = 2,4,6-trimethylthiophenolate and SCy = cyclohexanethiolate. X-ray crystal structures revealed that 1 and 2 possess trigonal bipyramidal geometries formed by the N4S ligand set. In each case, the thiolate ligand is positioned cis to an imidazole donor, replicating the arrangement of Cys- and His-based substrates in the active site of EgtB. The geometric and electronic structures of 1 and 2 were analyzed with UV-vis absorption and M?ssbauer spectroscopies in tandem with density functional theory (DFT) calculations. Exposure of 1 and 2 to nitric oxide (NO) yielded six-coordinate FeNO adducts that were characterized with infrared and electron paramagnetic resonance (EPR) spectroscopies, confirming that these complexes are capable of binding diatomic molecules. Reaction of 1 and 2 with O2 causes oxidation of the thiolate ligands to disulfide products. The implications of these results for the development of functional models of EgtB and OvoA are discussed. This journal is
- Ekanayake, Danushka M.,Fischer, Anne A.,Elwood, Maya E.,Guzek, Alexandra M.,Lindeman, Sergey V.,Popescu, Codrina V.,Fiedler, Adam T.
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- Lewis base-complexed magnesium dithiolenes
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The first magnesium-based dithiolene, 2, was prepared by reaction of the lithium dithiolene radical, 1, with 2-mesitylmagnesium bromide. Reaction of 2 with N-heterocyclic carbenes (in toluene) gave a carbene-stabilized magnesium monodithiolene complex, 3. Complex 3, in turn, is readily converted to a THF-solvated magnesium bis-dithiolene dianion, 4, via partial hydrolysis in polar solvents (i.e., THF/CH3CN). Compounds 2, 3 and 4 have been spectroscopically and structurally characterized and probed by DFT computations.
- Wang, Yuzhong,Maxi, Nirva A.,Xie, Yaoming,Wei, Pingrong,Schaefer, Henry F.,Robinson, Gregory H.
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- Synthesis and crystal structure of an arenesulfenyl iodide with unprecedented stability
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An arenesulfenyl iodide with unprecedented stability was synthesized by oxidation of a thiol bearing a novel bowl-type substituent with iodine, whose monomeric structure was determined by X-ray crystallographic analysis.
- Goto, Kei,Holler, Michel,Okazaki, Renji
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- Synthesis of Symmetrical Thiosulfonates via Cu(OTf)2-Catalyzed Reductive Homocoupling of Arenesulfonyl Chlorides
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A variety of symmetrical thiosulfonates are synthesized via Cu-catalyzed reductive homocoupling of aryl sulfonyl chlorides. This protocol uses organic amine acting as a mild reductant and low-cost copper as an effective catalyst. Such a reductive coupling process features a broad substrate scope and good functional group tolerance. Related thiosulfonate products can also be converted into diverse functional molecules.
- Liu, Lixia,Luo, Bo,Wang, Chengming
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supporting information
p. 5880 - 5883
(2021/11/27)
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- Transformation of arylboronic acids with sodium thiosulfate into organodisulfides catalyzed by a recyclable polyoxometalate-based Cr(iii) catalyst
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Organo disulfides represent an abundant class of compounds in chemical biology, pharmaceutical fields, and industry. They are traditionally synthesized by the oxidation of mercaptan in the presence of an organic ligand supported metal catalyst or toxic oxidants under harsh conditions. Here, we disclose a highly-efficient pathway in which disulfide is synthesized by organic boric acid and Na2S2O3 using the catalyst (NH4)3[CrMo6O18(OH)6], demonstrating a high activity and excellent selectivity. Various boric acid derivatives have been successfully transformed into the corresponding disulfides. Mechanistic insights have been furnished based on the observation of intermediate and control experiments.
- Chang, Yalin,Li, Huiyi,Tao, Chaofu,Wang, Aiping,Wei, Yongge,Xie, Ya,Yu, Han,Yu, Shunming
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supporting information
p. 6059 - 6064
(2021/08/23)
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- Synthesis of symmetrical / unsymmetrical thiosulfonates through the disproportionate coupling reaction of sulfonyl hydrazide mediated by phosphomolybdic acid
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Phosphomolybdic acid (H3PMo12O40) is reported as a green low-cost catalyst for the synthesis of symmetrical / unsymmetrical thiosulfonates via the disproportionate coupling reaction of sulfonyl hydrazide. The attributes of this reported catalytic system include low catalyst loadings (1 mol%), efficient turnover, and high yields (up to 94%). Additionally, this reaction mechanism involves the formation of a thiyl radical and sulfonyl radical via sulfinyl radical disproportionation.
- Lv, Mengting,Liu, Yufeng,Li, Ke,Yang, Guoping
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supporting information
(2021/01/21)
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- Chemoselective synthesis of diaryl disulfides via a visible light-mediated coupling of arenediazonium tetrafluoroborates and CS2
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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
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supporting information
p. 903 - 909
(2017/06/23)
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- Preparation of Propargylic Sulfinates and their [2,3]-Sigmatropic Rearrangement to Allenic Sulfones
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The scope of the [2,3]-sigmatropic rearrangement of propargylic sulfinates to allenic sulfones by silver catalysis was expanded. A series of new propargylic sulfinate esters was generated from a variety of aromatic and heteroaromatic sulfonyl chlorides an
- Tata, Rama Rao,Hampton, Carissa S.,Harmata, Michael
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supporting information
p. 1232 - 1241
(2017/04/11)
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- Tunable and Practical Synthesis of Thiosulfonates and Disulfides from Sulfonyl Chlorides in the Presence of Tetrabutylammonium Iodide
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A tunable and practical synthesis of electrophilic sulfenylating reagents, thiosulfonates and disulfides, from inexpensive and easily available sulfonyl chlorides, has been developed. By appropriate choice of solvents, the reaction of sulfonyl chlorides and tetrabutylammonium iodide gave the target products in good to excellent yields, respectively. These transformations probably proceed through a reducing–coupling pathway. (Figure presented.).
- Zheng, Yong,Qing, Feng-Ling,Huang, Yangen,Xu, Xiu-Hua
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supporting information
p. 3477 - 3481
(2016/11/13)
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- Electrophilic alkylation of pseudotetrahedral nickel(II) arylthiolate complexes
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A kinetic study is reported for reactions of pseudotetrahedral nickel(II) arylthiolate complexes [(TpR,Me)Ni-SAr] (TpR,Me = hydrotris{3-R-5-methyl-1-pyrazolyl}borate, R = Me, Ph, and Ar = C6H5, C6H4-4-Cl, C6H4-4-Me, C6H4-4-OMe, 2,4,6-Me3C6H2, 2,4,6-iPr3C6H2) with organic electrophiles R'X (i.e., MeI, EtI, BzBr) in low-polarity organic solvents (toluene, THF, chloroform, dichloromethane, or 1,2-dichloroethane), yielding a pseudotetrahedral halide complex [(TpR,Me)Ni-X] (X = Cl, Br, I) and the corresponding organosulfide R'SAr. Competitive reactions with halogenated solvents and adventitious air were also examined. Akin to reactions of analogous and biomimetic zinc complexes, a pertinent mechanistic question is the nature of the reactive nucleophile, either an intact thiolate complex or a free arylthiolate resulting from a dissociative pre-equilibrium. The observed kinetics conformed to a second-order rate law, first order with respect to the complex and electrophile, and no intermediate complexes were observed. In the absence of a mechanistically diagnostic rate law, a variety of mechanistic probes were examined, including kinetic effects of varying the metal, solvent, electrophile, and temperature, as well as the 3-pyrazolyl and arylthiolate substituents. Compared to zinc analogues, the effect of Ni-SAr covalency is also of interest herein. The results are broadly interpreted with respect to the disparate mechanistic pathways.
- Deb, Tapash,Jensen, Michael P.
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supporting information
p. 87 - 96
(2015/03/03)
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- Synthesis, structure and reactivity of Ni site models of [NiFeSe] hydrogenases
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A series of structural models of the Ni centre in [NiFeSe] hydrogenases has been developed which exhibits key structural features of the Ni site in the H2 cycling enzyme. Specifically, two complexes with a hydrogenase-analogous four-coordinate 'NiS3Se' primary coordination sphere and complexes with a 'NiS2Se2' and a 'NiS 4' core are reported. The reactivity of the complexes towards oxygen and protons shows some relevance to the chemistry of [NiFeSe] hydrogenases. Exposure of a 'NiS3Se' complex to atmospheric oxygen results in the oxidation of the selenolate group in the complex to a diselenide, which is released from the nickel site. Oxidation of the selenolate ligand on Ni occurs approximately four times faster than oxidation with the analogous sulfur complex. Reaction of the complexes with one equivalent of HBF4 results in protonation of the monodentate chalcogenolate and the release of this ligand from the metal centre as a thiol or selenol. Unrelated to their biomimetic nature, the complexes serve also as molecular precursors to modify electrodes with Ni-S-Se containing particles by electrochemical deposition. The activated electrodes evolve H2 in pH neutral water with an electrocatalytic onset potential of -0.6 V and a current density of 15 μA cm-2 at -0.75 V vs. NHE.
- Wombwell, Claire,Reisner, Erwin
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p. 4483 - 4493
(2014/03/21)
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- Use of base control to provide high selectivity between diaryl thioether and diaryl disulfide for C-S coupling reactions of aryl halides and sulfur and a mechanistic study
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Previous studies have reported that S-arylation produces diaryl disulfide when the precursors include sulfur powder and aryl halide using CuI as the catalyst. However, our research has revealed that the use of different bases in the above S-arylation process results in the coproduction of diarylsulfane and diaryldisulfane. In addition, we have demonstrated that the ratio of the two products can be controlled by selecting the alkalinity of the bases. 1H NMR spectra showed that diaryldisulfane was the first product, which became the reagent in a reaction with aryl halide to form diarylsulfane through CuI catalysis. Various aryl halides were tested to enhance the selectivity between diarylsulfane and diaryldisulfane using various different bases, leading to the following principles. A weak base, such as metal carbonate or acetate, results in the production of only diaryldisulfane; a strong base, such as metal hydroxide, results in the production of both diaryldisulfane and diarylsulfane. According to DFT calculations, hydroxide ions, which were exchanged for iodide and bonded with Cu, affected Cu electrons more strongly to reduce diaryl disulfide.
- Chen, Hsing-Ying,Peng, Wei-Te,Lee, Ying-Hsien,Chang, Yu-Lun,Chen, Yen-Jen,Lai, Yi-Chun,Jheng, Nai-Yuan,Chen, Hsuan-Ying
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supporting information
p. 5514 - 5522
(2013/11/06)
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- Methods for Preparing Diaryl Disulfides
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New and useful methods for preparing bulky diaryl disulfides from a benzene derivative and sulfur halide are disclosed.
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Page/Page column 5
(2012/06/30)
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- Efficient organic transformations mediated by ZrOCl28H 2O in Water
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Operationally simple and environmentally benign methods for some organic transformations comprising reductive coupling of sulfonyl chlorides, chemoselective deoxygenation of sulfoxides, and halogenation of alcohols mediated by ZrOCl28H2O/MX in water have been developed.
- Jafarpour, Maasoumeh,Rezaeifard, Abdolreza,Heidari, Mahdieh
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experimental part
p. 1470 - 1482
(2011/10/05)
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- Novel reduction of arylsulfonyl chlorides to disulfides with Sm/NiCl2/KI system
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Arylsulfonyl chlorides can be readily reduced to corresponding disulfides with Sm/NiCl2/KI system in moderate to good yields at 60°C.
- Zhan, Zhuangping,Guo, Hongyun,Zhang, Yongmin
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p. 2749 - 2752
(2007/10/03)
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- Novel reduction of sulfonyl halides to disulfides with SmI2/THF/HMPA system
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Sulfonyl halides can be readily reduced to corresponding disulfides with SmI2/THF/HMPA system in moderate to good yields at 60°C.
- Guo,Wang,Zhang
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- Pathways and Stereochemistry of Rearrangements in Reactions of Sulfenyl Chlorides with Alkenes
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In reactions of 3,3-dimethyl-1-butene and 3-methyl-1-butene with 2,4-dinitrobenzenesulfenyl chloride in the systems M(ClO4)n-CH3NO2 (M=Li or Mg), 1,2 shifts of the methyl group and hydride ion respectively occur directly within the AdE process (? pathway of the rearrangement).In the same systems reactions of these alkenes with arenesulfenyl chlorides containing in the electrophilic moiety less electronegative substituents, as compared to the dinitrophenyl group, initially yield β-chloro sulfides, which under reaction conditions mostly undergo rearrangements (? pathway of the rearrangement).In nitromethane in the presence of LiClO4, AlCl3, or AgBF4 erythro-2-arylthio-1-chloro-1-deutero-2,3-dimethylbutanes are converted into stereoisomeric thiochromans; their ratio is controlled by the nature of the metal compound added, electronic properties of substituents in the arylthio moiety, and reaction temperature.
- Borisov, A. V.,Bodrikov, I. V.,Borisova, G. N.,Smit, V. A.,Lutsenko, A. I.,Bel'skii, V. K.
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p. 943 - 951
(2007/10/03)
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- RADIKALIONEN 89. EINELEKTRONEN-OXIDATIONEN VON DIARYLDISULFIDEN MIT AlCl3/H2CCl2
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The single electron oxidation of 14 alkyl and alkoxy substituted diaryldisulfides by AlCl3/H2CCl2 has been investigated by ESR/ENDOR spectroscopy.The radical cations observed prove the following skeletal rearrangements: Those with ring hydrogens in ortho positions to the disulfide bridge preferentially form thianthrene derivatives.The isomeric dinaphthyl disulfides react differently, the 2,2'-isomer yielding the dibenzothianthrene radical cation and the 1,1'-isomer the well-known naphthalene-1,8-disulfide radical cation.For all diaryl disulfides with completely alkyl- or methoxy-blocked ortho positions, oxidative desulfuration is observed.As substantiated by additional (2)D and (33)S isotope marking, the bis(2,5-dimethoxyphenyl)disulfide reacts both to the corresponding thianthrene derivative as well as via desulfuration to the radical cation of the monosulfide.Accompanying cyclovoltammetric and photoelectron spectroscopic measurements prove that all ESR spectroscopically detected radical cations result from compounds Ar-S-Ar, Ar-SS-Ar and Ar(S)2Ar with rather low oxidation or ionisation potentials and thus suggest that each the most easily oxidized paramagnetic species is observed in the rather complex product mixtures, which form on AlCl3/H2CCl2 oxidation of diaryldisulfides. Key words: Diaryl disulfides; one-electron oxidation; radical cations; ESR/ENDOR spectra.
- Bock, Hans,Rittmeyer, Peter
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p. 261 - 292
(2007/10/02)
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- Radical Ions, 81. ENDOR Spectroscopic Investigations of Radical Cations of Aromatic Organosulfur Compounds
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Conditions for ENDOR measurements of organosulfur radical cations are discussed and tested.The one electron oxidation of a variety of aromatic sulfur compounds comprising benzene-1,2-dithiole, 1,4-dithiine, thianthrene and diphenylsulfide derivatives as well as 33S isotope-marked bis(2,5-dimethoxyphenyl)disulfide is accomplished using the oxygen-free, powerful and selective AlCl3/H2CCl2 reagent.Partly with substantial structural changes, paramagnetic M.+ species of 1,2-benzodithiete, 1,4-dithiine, thianthrene and diphenyl sulfide result.Their temperature-dependent ENDOR signal patterns provide numerous information e.g. on radical cation structure and dynamics, on the rather high sulfur spin populations or on the spin rotation interaction dominated relaxation behaviour.Accordingly, to obtain optimum ENDOR effects in organosulfur radical cations low temperature measurements are required, and especially for still undiscovered 33S ENDOR couplings, small g factor anisotropies and 33S spin densities appear to be necessary. - Keywords: ENDOR (Special, General Triple) Spectra, Temperature Dependence, Organosulfur Radical Cations, Structural Changes, Molecular Dynamics
- Bock, H.,Hierholzer, B.,Rittmeyer, P.
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p. 187 - 204
(2007/10/02)
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- The Invention of New Radical Chain Reactions. Part 11. A New Method for the Generation of Tertiary Radicals from Tertiary Alcohols
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A convenient procedure for the radical deoxygenation of tertiary alcohols has been invented using the double half esters of oxalic acid with the t-alcohol and N-hydroxypyridine-2-thione.Decomposition of this type of ester in the presence of 1,1-dimethylethane- or (better) 1,1-diethylpropane-thiol gave the corresponding hydrocarbons in good yield.It has been shown that the oxalate fragmentation is not concerted, but involves a stepwise loss of carbon dioxide.Tertiary alcohols are also a convenient source of radicals for addition to siutable alkenes with formation of quaternary centres.
- Barton, Derek H. R.,Crich, David
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p. 1603 - 1612
(2007/10/02)
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- The co-oxidation reaction of isoprene and some aromatic thiols
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The co-oxidation reaction between isoprene, some aromatic thiols and molecular oxygen is described.The product distribution, in relation to the nature of the aromatic thiol used, is examined.Steric and electronic factors are discussed.
- Laan, R. van der,Moolenaar, M.J.,Koning, H. de,Huisman, H.O.
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p. 220 - 225
(2007/10/02)
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- Photoreactions of β-Ketosulphides: Aryl and Benzyl Phenacyl Sulphides and Related Compounds
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Photoreactions of aryl phenacyl sulphides were studied, particularly in regard to substituent and solvent effects.In general, aryl phenacyl sulphides Ar1SCH2COAr2 1 = p-tolyl, Ar2 = p-X-C6H4 (X = H, Cl, OH, OMe, and Ph), 2-thienyl, and 2-furyl; Ar1 = 2,4,6-trimethylphenyl, Ar2 = Ph and p-HOC6H4; Ar1 = 2-benzthiazolyl, Ar2 = Ph> underwent photochemical cleavage to disulphides (Ar1S)2 and ketones Ar2COMe.In a few cases a diketone (Ar2COCH2)2 was the only, or major, carbonyl photoproduct.Similar photochemical behaviour was shown by ketosulphides p-Me-C6H4SCH(R)COPh (R = PhCH2, PhCOCH2, and p-Me-C6H4S) and related acetophenone derivatives PhCOCH2SR (R = COPh, SO3Na, and SCH2COPh).In a few instances, from p-Me-C6H4SCH2COAr (Ar = Ph, p-Cl-C6H4, and p-Ph-C6H4), a minor photoproduct was a 2-aryl-5-methylbenzothiophen.Benzyl phenacyl sulphides p-X-C6H4COCH2SCH2Ph (X = OH and OMe) also underwent photo-cleavage to give dibenzyl disulphide and a ketone.Free-radical cleavage products ArCOCH2(.) (Ar = Ph and p-MeO-C6H4) and p-Me-C6H4S(.) were trapped as adducts p-Me-C6H4SC(Ph)2CH2CH2COAr when irradiation of the ketosulphide was carried out in the presence of 1,1-diphenylethylene. 2,5-Diphenylfuran was formed photochemically from 1,4-diphenylbutane-1,4-dione on irradiation in methanol.
- Arora, Kanwar J. S.,Collier, John R.,Deodhar, Dinker J.,Hesabi, Masoud-M.,Hill, John
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p. 2148 - 2183
(2007/10/02)
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- A New Method for the Radical Deoxygenation of Tertiary Alcohols
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Tertiary alcohols can be deoxygenated in a radical chain reaction based on their mixed oxalate esters with N-hydroxy-2-thiopyridone, these esters being obtained directly from the alcohols and oxalyl chloride etc. or via their trimethylsilyl derivatives.
- Barton, Derek H. R.,Crich, David
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p. 774 - 775
(2007/10/02)
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- BIOMIMETIC REDUCTION OF SULFURIC ACID.
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Sulfuric acid and sodium sulfate were readily reduced to elemental sulfur and hydrogen sulfide upon treatment with a mixture of either one of polyphosphoric acid derivatives, PPE, PPA, and P//4O//1//0, which can form a mixed anhydride having -P-O-S- linkage, and iodide or thiol. Sulfur dioxide, which is undoubtedly one of the important intermediates, was trapped by p-tolyllithium to afford p-toluenesulfinic acid which was converted to p-tolyl methyl sulfone upon treatment with methyl iodide, though the yield was low. Sulfur trioxide which has been postulated as the key intermediate in the biological reduction of inorganic sulfate, was also trapped by mesitylene to give mesitylenesulfonic acid in a high yield. The reduction of sulfate to elemental sulfur and hydrogen suylfide is considered to proceed through the course which resembles the biological reaction path involved in the assimilatory metabolism of inorganic sulfate in microorganisms and plants.
- Oae,Togo
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p. 3818 - 3823
(2007/10/02)
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- KINETIC RESOLUTION OF RACEMIC SULPHILIMINES BY ENANTIOSELECTIVE REDUCTION WITH ARENETHIOLS CATALYZED BY CHIRAL AMINES
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S-Methyl-S-p-tolyl- and S-ethyl-S-p-tolyl-N-tosylsulphilimine can be obtained in optically active form by enantioselective reduction of their racemic mixture with arenethiols catalyzed by chiral amines.
- Dell'Erba, Carlo,Novi, Marino,Garbarino, Giacomo,Corallo, Poluzzi Giancarla
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p. 1191 - 1192
(2007/10/02)
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- DISULFIDES BY REDUCTION OF THIOSULFONIC S-ESTERS
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Disulfides are smoothly prepared from thiosulfonic S-esters by chlorotrimethylsilane and sodium iodide.In addition, thiosulfonic S-esters have been shown to be probable intermediates in other already known reactions leading to disulfides.
- Palumbo, Giovanni,Parrilli, Michelangelo,Neri, Orsola,Ferreri, Carla,Caputo, Romualdo
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p. 2391 - 2394
(2007/10/02)
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- Synthesis of S-Substituted Benzils and Some Hindered Biphenyls
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Three methylthio and/or methylsulfinyl substituted benzils (2, 6 and 7) have been synthesized on photo- or thermochemical routes, respectively.Photodecarboxylation of some new different substituted mesityl benzoates (1a-e) leads to hindered biphenyls (3a-e) accompanied sometimes by aldehyde (4a-c) and benzil formation (2) due to compatitive α-cleavage and subsequent stabilization processes of such generated free aroyl radicals.A short summary on constitutional conditions for intramolecular photoredox reactions of ortho functionalized aryl sulfinyl compounds is presented. - Keywords: Photodecarboxylations, α-Cleavages, Photoredox Reactions, Sulfoxides
- Luedersdorf, Reinhard,Mai, Juergen,Praefcke, Klaus
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p. 1420 - 1425
(2007/10/02)
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- FACILE REDUCTION OF SULFINIC ACID TO DISULFIDE WITH THIOL AND CHLOROTRIMETHYLSILANE
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Sulfinic acids were found to be readily reduced to the corresponding disulfide quantitatively at room temperature upon treatment with a mixture of thiols and chlorotrimethylsilane.
- Oae, Shigeru,Togo, Hideo,Numata, Tatsuo,Fujimori, Ken
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p. 1193 - 1196
(2007/10/02)
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