10490-07-0Relevant articles and documents
A very useful and mild method for the deoxygenation of sulfoxide to sulfide with silica bromide as heterogeneous promoter
Mohanazadeh, Farajollah,Veisi, Hojat,Sedrpoushan, Alireza,Zolfigol, Mohammad Ali,Golmohammad, Fereshteh,Hemmati, Saba,Hashemi, Majid
, p. 7 - 13 (2014/01/06)
Silica bromide (SB) as heterogeneous reagent and promoter is prepared from reaction of silica gel with PBr3 as a non-hydroscopic, filterable, cheap, and stable yellowish powder that can be stored for months. The results show that the SB is suitable and efficient reagent for deoxygenation of sulfoxides to the corresponding sulfides under mild conditions at room temperature. The easy availability of this reagent makes this simple procedure attractive and a practical alternative to the existing methods.
Kinetic resolution of α-bromophenylacetamides using quinine or Cinchona alkaloid salts
Marzorati, Liliana,Fejfar, Jose L.,Tormena, Claudio F.,Vitta, Claudio Di
experimental part, p. 748 - 753 (2012/09/05)
The kinetic resolution of racemic α-bromophenylacetamides 1 was achieved in the presence of benzenethiolate and Cinchona alkaloid salts as phase-transfer catalysts or benzenethiol and quinine, yielding (S)-enantioenriched α-sulfanylated products. The observed stereoselection was rationalized on the basis of the best fitting of 1 and the resolving agent in the ternary complexes.
Halogen-lithium exchange versus deprotonation: regioselective mono- and dilithiation of aryl benzyl sulfides. A simple approach to α,2-dilithiotoluene equivalents
Kli?, Tomasz,Serwatowski, Janusz,Wesela-Bauman, Grzegorz,Zadrozna, Magdalena
experimental part, p. 1685 - 1689 (2010/06/13)
Halogen-lithium exchange and deprotonation reactions between aryl benzyl sulfides and alkyllithiums were investigated. The resultant mono- and dilithiated intermediates were converted into the corresponding aldehydes and boronic, or carboxylic acids in good yields. It was found that diethyl ether stabilizes the ortho-lithiated compounds toward isomerisation to the benzylic derivatives. The process occurs easily in THF at low temperature and is a facile route to the α,2-dilithiotoluene derivative which can be transformed into a dicarboxylic acid on treatment with CO2.
Sulfur radical cations. Kinetic and product study of the photoinduced fragmentation reactions of (phenylsulfanylalkyl)trimethylsilanes and phenylsulfanylacetic acid radical cations
Baciocchi, Enrico,Giacco, Tiziana Del,Elisei, Fausto,Lapi, Andrea
, p. 853 - 860 (2007/10/03)
Laser and steady-state photolysis, sensitized by NMQ+, of PhSCH(R)X 1-4 (R = H, Ph; X =SiMe3, CO2H) was carried out in CH3CN. The formation of 1+.-4+. was clearly shown. All radical cations undergo a fast first-order fragmentation reaction involving C-Si bond cleavage with 1+. and 2+. and C-C bond cleavage with 3+. and 4+.. The desilylation reaction of 1+. and 2+. was nucleophilically assisted, and the decarboxylation rates of 3+. and 4+. increased in the presence of H2O. A deuterium kinetic isotope effect of 2.0 was observed when H2O was replaced by D2O. Pyridines too were found to accelerate the decarboxylation rate of 3+. and 4 +.. The rate increase, however, was not a linear function of the base concentration, but a plateau was reached. A fast and reversible formation of a H-bonded complex between the radical cation and the base is suggested, which undergoes C-C bond cleavage. It is probable that the H-bond complex undergoes first a rate determining proton-coupled electron transfer forming a carboxyl radical that then loses CO2. The steady-state photolysis study showed that PhSCH3 was the exclusive product formed from 1 and 3 whereas [PhS(Ph)CH-]2 was the only product with 3 and 4.
A Convenient Method for Preparation of 2-(Methylthio)alkanoic Acids and Their Related Compounds Using the Carbanions of Substituted Malonic Esters
Ogura, Katasuyuki,Itoh, Hiroshi,Morita, Toshio,Sanada, Kunio,Iida, Hirotada
, p. 1216 - 1220 (2007/10/02)
Starting from alkyl- or aryl-substituted malonic esters prepared by various methods, 2-(methylthio)alkanoic acids are synthesized by successive treatment with sodium ethoxide and with S-methyl methanethiosulfonate, followed by alkaline hydrolysis which causes concurrent decarboxylation.Production of 2-(phenylthio)alkanoic acids is also achieved in a similar manner.
