599-94-0Relevant academic research and scientific papers
Cycloaddition Reactions of Azides and Electron-Deficient Alkenes in Deep Eutectic Solvents: Pyrazolines, Aziridines and Other Surprises
Casarrubios, Luis,Díez-González, Silvia,Lachhani, Kushal,Pimpasri, Chaleena,Rzepa, Henry S.,Sebest, Filip,White, Andrew J. P.
, (2020/05/19)
The reaction of organic azides and electron-deficient alkenes was investigated in a deep eutectic solvents. A series of highly substituted 2-pyrazolines was successfully isolated and their formation rationalised by DFT calculations. The critical effect of substitution was also explored; even relatively small changes in the cycloaddition partners led to completely different reaction outcomes and triazolines, triazoles or enaminones can be formed as major products depending on the alkene employed. (Figure presented.).
Synthesis of alkyl aryl sulfones via reaction of N-arylsulfonyl hydroxyamines with electron-deficient alkenes
Bin, Yunhui,Hua, Ruimao
, (2017/01/24)
Alkyl aryl sulfones were prepared in high yields via the reaction of N-arylsulfonyl hydroxylamines with electron-deficient alkenes. These reactions have the advantages of simplicity, easily available starting materials and mild reaction conditions.
Method for preparing substituted ethyl aryl sulfone
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Paragraph 0085-0086, (2017/03/23)
The invention discloses a method for preparing substituted ethyl aryl sulfone. The method comprises the following steps: a compound shown in a formula II, a compound shown in a formula III and alkali are uniformly mixed in a solvent and are subjected to a coupling reaction, a compound shown in a formula I containing R2' as -CH2CH2R is obtained after the reaction is complete; or the method comprises the following steps: the compound shown in the formula II, ethyl propiolate and alkali are uniformly mixed in the solvent and then are subjected to the coupling reaction, and the compound shown in a formula I containing R2' as -CH=CH2=OOCH2CH3 is obtained after the reaction is complete. The method has the advantages of universality, convenience, simple reaction system, and mild reaction condition; the reaction can be amplified to a gram level, the reaction raw materials are simple and easily available, the used alkali and raw materials have the advantages of low cost and easy acquisition, the atom utilization rate is high, and solvent toxicity is low.
Efficient synthesis of γ-keto sulfones by NHC-catalyzed intermolecular Stetter reaction
Bhunia, Anup,Yetra, Santhivardhana Reddy,Bhojgude, Sachin Suresh,Biju, Akkattu T.
supporting information; experimental part, p. 2830 - 2833 (2012/07/17)
The N-heterocyclic carbene-catalyzed intermolecular Stetter reaction of aldehydes with α,β-unsaturated sulfones allows the atom-economic and selective formation of γ-keto sulfones in good yields. Key to the success of this unique transition-metal-free carbon-carbon bond-forming reaction is the right choice of the NHC precursor and base. The reaction tolerates a broad range of different aldehydes.
Binuclear manganese complexes as catalysts in the selective and efficient oxidation of sulfides to sulfones
Barton, Derek H. R.,Li, Wenge,Smith, Jason A.
, p. 7055 - 7058 (2007/10/03)
The binuclear Mn(IV)-Mn(IV) manganese complex 1 catalyzes the periodic acid oxidation of sulfides to sulfones under mild conditions. The reaction was found to be highly selective giving almost quantitative yields of the sulfones even in the presence other easily oxidized groups. Only amines were found to hinder the reaction.
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)+
Pihlaja, Kalevi,Kabilan, Senthamaraikannan,Ganapathi, Athiappan,Sankar, Punnaivanam
, p. 601 - 612 (2007/10/03)
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.
INNOVATIVE APPROACH TO THE SYNTHESIS OF SULPHIDES AND THEIR CORRESPONDING SULPHONES
Abd-El-Aziz, Alaa S.,Epp, Karen M.,Lei, Yun,Kotowich, Steven
, p. 1252 - 1286 (2007/10/02)
A general and efficient synthetic approach to aryl-aryl bis-sulphides with aliphatic or aromatic bridges via the nucleophilic aromatic substitution (SNAr) of cyclopentadienyliron arene complexes with a number of dithiols followed by photolytic demetallation is presented in this work.The oxidation of the bis(cyclopentadienyliron) arene complexes containing bis-sulphide linkages with 3-chlorobenzoic acid gave their corresponding sulphones in very good yield (70-95percent).Mixed ether/sulphide and ether/sulphone complexes were also prepared following the same synthetic strategy.Reactions of sulphide and sulphone diiron complexes with terminal chloro groups with a number of oxygen, sulphur and carbon nucleophiles allowed for the functionalization of these complexes.The use of photolytic demetallation as a means of liberating the modified arene ligands proved to be very successful.The mild conditions, high yields and low cost of the starting iron complexes make this method one of the most general and practical routes to sulphide and sulphone compounds.
Reactivity in Z-Philic Displacements in α-Halogenosulfones
Vernon, Adam,Stirling, Charles J. M.
, p. 1609 - 1610 (2007/10/02)
Rates of Z-philic reactions in β-substituted α-bromosulfones have been measured; for displacement-protonation ρ* = 2.9, and isotope fractionation factors close to 2.4 demonstrate extensive C-protonation in the transition structure.
Dipole Moments and UV Spectra of some Long-chain Molecules
Baliah, V.,Aparajithan, K.
, p. 255 - 259 (2007/10/02)
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.
Distinguishing between Polar and Electron-Transfer Mechanisms for Reactions of Anions with Alkyl Halides
Bordwell, F. G.,Wilson, Craig A.
, p. 5470 - 5474 (2007/10/02)
9-Substituted fluorenide carbanions in the series 9-MeFl-, 9-MeO-Fl-, and 9-Me2N-Fl-, which have nearly the same basicities but become progressively easier to oxidize, were selected as a test trio to probe for electron-transfer (eT-) components or radical-pair intermediates in reactions with alkyl halides.The trio members were shown to undergo eT- at progressively faster rates (>102 rate span) with two different types of single-electron acceptors, as expected- On the other hand, with PhCH2Cl, i-BuBr, or i-BuI, SN2 products were formed in a rate order that was the reverse of that established as characteristic of eT-.Reactions of the more sterically hindered 9-i-Pr2N-Fl- ion with PhCH2Cl or i-BuI to give SN2 products were over 1400 times slower than those with 9-MeFl-, whereas the eT- rate with c-C6H10(NO2)Ts was eight times faster.On the other hand, reactions of the test trio with F3CCH2I, which is known to react slowly in SN2 reactions, gave the reactivity order characteristic of eT-, and radical-type products were formed.For this reaction, a plot of log kobsd vs.Eox(A-) for seven 9-G-Fl- ions, wherein the bulk and radical-stabilizing ability of G was varied, was linear.This result shows that Eox(A-) is a good measure of eT- ability and that eT- rates are insensitive to steric effects in either the donor or acceptor that cause larger rate retardations in polar SN2 reactions.
