- Synthesis and characterization of dithioethers, and their RuII and RuIII complexes
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The syntheses of nine, new dithioethers of the type RS(CH2)xSR, where x = 2 or 3 and R is an alkyl chain, as well as the known x = 2, R = phenyl or cyclohexyl compounds, are reported. The known dithioethers react with RuCl3·3H2O to form trans-RuCl2(dithioether)2 complexes 1 (R = Ph) and 2 (R = C6H11), whereas from the other dithioethers RuCl2[RS(CH2)xSR]2(μ-Cl)2 complexes have been isolated, where x = 3, and R = Et (complex 3), nPr (complex 4), nBu (complex 5), and R = npentyl (complex 6). The complexes are well characterized, including X-ray structures for complexes 1–4. The interest in these compounds stems from oxidation of the dithioethers to the corresponding disulfoxides and their Ru complexes.
- Cheu, Elizabeth L.S.,Yapp, Donald T.T.,Patrick, Brian O.,James, Brian R.
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- One-Pot Copper-Catalysed Thioetherification of Aryl Halides Using Alcohols and Lawesson's Reagent in Diglyme
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A new protocol for the thioetherification of structurally varied alcohols with aryl halides using Lawesson's reagent, catalysed by copper(I) iodide, and using diglyme as a safe solvent was developed. Using this method, the reactions of aryl halides proceeded efficiently, and the desired sulfides were obtained in high to excellent yields. The method uses alcohols as starting materials, which is a significant advantage over methods that start from thiols. Alcohols are widely commercially available in a much greater structural diversity than thiols, and they are also nontoxic and not foul-smelling. A reaction mechanism was proposed. A copper-catalysed method for the thioetherification of alcohols with aryl halides using Lawesson's reagent was developed.
- Gholinejad, Mohammad
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p. 4162 - 4167
(2015/06/30)
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- Silica: An efficient catalyst for one-pot regioselective synthesis of dithioethers
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The development of a silica-promoted highly selective synthesis of 1,2 or 1,3-dithioethers via solvent-free one-pot tandem reactions of an allyl bromide with excess thiol at room temperature is described. The choice of silica gel, either pre-calcined or moistened with water, exhibited notable regioselectivity in the formation of dithioethers. Plausible mechanistic routes were explored and postulated.
- Kundu, Samir,Roy, Babli,Basu, Basudeb
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- Silica nanoparticles as a reusable catalyst: A straightforward route for the synthesis of thioethers, thioesters, vinyl thioethers and thio-Michael adducts under neutral reaction conditions
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A simple and straightforward route for the synthesis of thioethers, thioesters, vinyl thioethers and thio-Michael adducts has been demonstrated using silica nanoparticles (NPs) as a reusable catalyst via the 1,2-addition of thiols to alkenes, alkynes and alkyl/acyl halides, and the 1,4-addition of thiols to conjugated alkenes at room temperature.
- Banerjee, Subhash,Das, Jayanta,Alvarez, Richard P.,Santra, Swadeshmukul
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experimental part
p. 302 - 306
(2010/06/13)
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- Native silica nanoparticle catalyzed anti-Markovnikov addition of thiols to inactivated alkenes and alkynes: a new route to linear and vinyl thioethers
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A new route for the synthesis of linear and vinyl thioethers has been demonstrated using bare silica nanoparticle as catalyst at room temperature under solvent-free conditions. The catalyst can be reused up to six times without loss of catalytic activity.
- Banerjee, Subhash,Das, Jayanta,Santra, Swadeshmukul
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scheme or table
p. 124 - 127
(2009/04/14)
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- 1H- And13C-NMR and electron ionization (EI) mass spectrometric study of o- And p-substituted 1,n-diarylsulfonylalkanes, XC6H4so2(CH2)nso 2C6H4X (n = 2-5, 8, 10)+
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1,n-Diphenylsulfonylalkanes, PhSO2(CH2)nSO2Ph (n =2-5, 8, 10) and their o- or p-Cl or -OMe derivatives were prepared and their 1H- and 13C-NMR and EI mass spectra recorded and analyzed. The chemical shifts of the aliphatic α- and β-carbons showed a clear dependence on the o-aryl substitution, the o-Cl being the most shielding for both. Clear low-field effects were found also for the aliphatic α-protons in o-Cl and o-OMe derivatives. In case of p-OMe derivatives a palpable shielding of the aliphatic α-protons was also found similarly to the β-protons of the o-OMe derivatives. Characteristic mass spectrometric fragmentations which reflected both the influence of the aryl substitution and the length of the alkyl chain were observed and sometimes also exhibited the sulphinic acid rearrangement.
- Pihlaja, Kalevi,Kabilan, Senthamaraikannan,Ganapathi, Athiappan,Sankar, Punnaivanam
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p. 601 - 612
(2007/10/03)
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- Dipole Moments and UV Spectra of some Long-chain Molecules
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About one hundred compounds with long-chain molecular structure have been prepared (most of them are new).The dipole moments of four α,ω-bis(p-methoxyphenylthio)alkanes and five α,ω-bis(p-methoxyphenylsulphonyl)alkanes have been determined to find the effect of chain-length.In the case of sulphones, the observed values are compared with the values calculated for free rotation around all bonds intervening the end dipoles.The uv spectra of some 1,2-(distyrylsulphonyl)ethanes, and a number of α,ω-bis(arylsulphonyl)- and α,ω-bis(aryloxy)alkanes have been recorded to examine the applicability of the principle of chromophore additivity.
- Baliah, V.,Aparajithan, K.
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p. 255 - 259
(2007/10/02)
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- Novel Alumina-catalysed Reactions of Arylthioalkyl Halides and Related Compounds
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Arylthioalkyl halides of the type ArS(CH2)nCl (Ar = phenyl or substituted phenyl, n = 1-4) undergo rearrangement on heating with neutral alumina to 1,n-bis(arylthio)alkanes of type ArS(CH2)nSAr in high yield.Similar rearrangements occur with some closely related structural types.The bis(arylthio)alkanes undergo further reaction with alumina at higher temperatures in air giving diaryl disulphides.Bis(o-iodophenylthio)methane eliminates iodine on heating with alumina, producing dibenzodithiepin.Some observations concerning the mechanism are presented.
- Jigajinni, Veerappa B.,Wightman, Richard H.
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p. 1801 - 1812
(2007/10/02)
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- Novel Alumina-catalysed Reactions of Arylthioalkyl Halides
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ω-Chloroalkyl aryl sulphides rearrange to αω-bisaryl thioalkanes on treatment with alumina, and an alumina-catalysed equivalent of the Ullmann biphenyl synthesis is reported.
- Jigajinni, Veerappa B.,Wightman, Richard H.,Campbell, Malcolm M.
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