3238-95-7Relevant articles and documents
Acid/Phosphide-Induced Radical Route to Alkyl and Alkenyl Sulfides and Phosphonothioates from Sodium Arylsulfinates in Water
Lin, Ya-Mei,Lu, Guo-Ping,Wang, Gui-Xiang,Yi, Wen-Bin
, p. 382 - 389 (2017/04/26)
A newly developed aqueous system with acid and phosphide was introduced in which odorless and stable sodium arylsulfinates can in situ generate arylsulfenyl radicals. These radicals have high reactivity to react with alkynes, alkenes, and H-phosphine oxides for the synthesis of alkyl and alkenyl sulfides and phosphonothioates. The control experiments and quantum calculations are also performed to gain insights into the generation mechanism of arylsulfenyl radicals. Notably, the chemistry is free of thiol odors, organic solvents, and metals.
A highly efficient heterogeneous rhodium(I)-catalyzed C-S coupling reaction of thiols with polychloroalkanes or alkyl halides under mild conditions
Xia, Jianhui,Yao, Ruiya,Cai, Mingzhong
, p. 221 - 225 (2015/03/30)
Heterogeneous C-S coupling reaction of thiols with polychloroalkanes or alkyl halides was achieved at 30 or 80 °C in the presence of 5 mol% of an MCM-41-immobilized bidentate phosphine rhodium complex (MCM-41-2P-RhCl(PPh3)) and triethylamine, yielding a variety of formaldehyde dithioacetals, ethylenedithioethers and unsymmetric thioethers in good to excellent yields. This heterogeneous rhodium catalyst can be easily recovered and recycled by simple filtration of the reaction solution and used for at least 10 consecutive trials without significant loss of activity.
Rhodium-catalyzed reaction of thiols with polychloroalkanes in the presence of triethylamine
Tanaka, Ken,Ajiki, Kaori
, p. 1537 - 1539 (2007/10/03)
(Chemical Equation Presented) RhCl(PPh3)3 catalyzes a reaction of thiols with polychloroalkanes in the presence of triethylamine. This reaction serves as a convenient new method to produce formaldehyde dithioacetals, ethylenedithioethers, thioformates, and dithiocarbonic esters under mild conditions.
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.
MODERN FRIEDEL-CRAFTS CHEMISTRY. XIV. ON THE CYCLIZATION OF SELECTED ARYL HYDROXYALKYL SULFIDES
El-Khawaga, A. M.,El-Zohry, M. F.,Ismail, M. T.,Abdel-Wahab, A. A.,Khalaf, A. A.
, p. 265 - 270 (2007/10/02)
The feasibility of cycloalkylation reactions in the presence of Friedel-Crafts catalysts was demonstrated in a nimber of aryl hydroxyalkyl sulfides (1-5), and benzyl hydroxyalkyl sulfides (6-7).Treatment of compounds (1-7) with Friedel-Crafts catalysts gave diaryl disulfides, diaryl sulfides, arene thiols, chlorohydrins, aryl chloroalkyl sulfides, aryl alkenyl sulfides and cyclization products.It is noteworthy to mention that cyclization products were isolated only in cases where the hydroxyl group is linked to a tertiary carbon atom as in compounds 3 and 7.A suitable reaction pathway is suggested to rationalize the formation of the various reaction products.
Novel Alumina-catalysed Reactions of Arylthioalkyl Halides and Related Compounds
Jigajinni, Veerappa B.,Wightman, Richard H.
, p. 1801 - 1812 (2007/10/02)
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.
REAKTION VON 2-ARYLMERCAPTOETHYLHALOGENIDEN MIT MAGNESIUM BZW. ALKALICYANIDEN
Salbeck, Gerhard
, p. 165 - 168 (2007/10/02)
By reaction of 2-arylmercaptoethylhalogenides with magnesium the main reaction products are 1,2-bisarylmercapto-ethanes.The same products are obtained in nearly quantitative yield by reaction of 2-arylmercaptoethylhalogenides with alkalicyanides. 2-arylmercaptopropionitrils can not be synthesized according to the procedure described.