20875-34-7Relevant academic research and scientific papers
Preparation of Propargylic Sulfinates and their [2,3]-Sigmatropic Rearrangement to Allenic Sulfones
Tata, Rama Rao,Hampton, Carissa S.,Harmata, Michael
supporting information, p. 1232 - 1241 (2017/04/11)
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
Methods for Preparing Diaryl Disulfides
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Page/Page column 4-5, (2012/06/30)
New and useful methods for preparing bulky diaryl disulfides from a benzene derivative and sulfur halide are disclosed.
Discovery of 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride as a deoxofluorinating agent with high thermal stability as well as unusual resistance to aqueous hydrolysis, and its diverse fluorination capabilities including deoxofluoro-arylsulfinylation with high stereoselectivity
Umemoto, Teruo,Singh, Rajendra P.,Xu, Yong,Saito, Norimichi
supporting information; experimental part, p. 18199 - 18205 (2011/03/18)
Versatile, safe, shelf-stable, and easy-to-handle fluorinating agents are strongly desired in both academic and industrial arenas, since fluorinated compounds have attracted considerable interest in many areas, such as drug discovery, due to the unique effects of fluorine atoms when incorporated into molecules. This article describes the synthesis, properties, and reactivity of many substituted and thermally stable phenylsulfur trifluorides, in particular, 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride (Fluolead, 1k), as a crystalline solid having surprisingly high stability on contact with water and superior utility as a deoxofluorinating agent compared to current reagents, such as DAST and its analogues. The roles of substiuents on 1k in thermal and hydrolytic stability, fluorination reactivity, and the high-yield fluorination mechanism it undergoes have been clarified. In addition to fluorinations of alcohols, aldehydes, and enolizable ketones, 1k smoothly converts non-enolizable carbonyls to CF2 groups, and carboxylic groups to CF3 groups, in high yields. 1k also converts C(=S) and CH3SC(=S)O groups to CF2 and CF3O groups, respectively, in high yields. In addition, 1k effects highly stereoselective deoxofluoro-arylsulfinylation of diols and amino alcohols to give fluoroalkyl arylsulfinates and arylsulfinamides, with complete inversion of configuration at fluorine and the simultaneous, selective formation of one conformational isomer at the sulfoxide sulfur atom. Considering the unique and diverse properties, relative safety, and ease of handling of 1k in addition to its convenient synthesis, it is expected to find considerable use as a novel fluorinating agent in both academic and industrial arenas.
An easy and practical synthesis of symmetrical thiosulfonic S-esters
Chemla, Fabrice
, p. 894 - 896 (2007/10/03)
Symmetrical alkyl and aryl thiosulfonic S-esters were prepared in good to excellent yields by the acetyl chloride-activated zinc reduction of sulfonyl chlorides.
PREPARATION AND SPECTRAL PROPERTIES OF SYMMETRICAL S-ARYL ARENESULFONOTHIOATES (THIOSULFONATES)
Freeman, Fillmore,Bartosik, Lisa G.,Bui, Nghe Van,Keindl, Monica C.,Nelson, Eric L.
, p. 375 - 386 (2007/10/02)
Arenesulfinyl chlorides (4-XC6H4S(O)Cl; X = H, CH3, F, Cl, Br) react with activated zerovalent zinc in benzene at 6 to 8 deg C to give symmetrical S-aryl arenesulfonothioates (thiosulfonates) in good to excellent yields. 2- and 3-substituted arenesulfinyl chlorides (X=Cl, CH3) give a mixture of products (disulfide, thiosulfinate, and/or thiosulfonate). 2,4,6-Triisopropylbenzenesulfinyl chloride reacts with zinc in 1,2-dimethoxyethane to give S-(2,4,6-triisopropylphenyl) 2,4,6-triisopropylbenzenesulfinothioate and bis(2,4,6-triisopropylphenyl) disulfide.Possible mechanisms for the reaction, the 1H and 13C NMR spectra and the chemical ionization and electron impact mass spectra of the thiosulfonates are discussed.The para carbon substituent chemical shifts (Cp-SCS) for the thiosulfonates and for symmetrical diaryl disulfides have been subjected to several dual substituent parameter (DSP) correlations. Key Words: S-aryl-arenesulfonothioates (thiosulfonates); arenesulfinyl chlorides; 1H and 13C NMR; mass spectrometry; substituent shift parameters.
Attempts to Synthesize Sterically Hindered Thiazyl Arenes and Their Relationship to Arylsulfenyl Nitrenes
Mayer, R.,Decker, D.,Bleisch, S.,Domschke, G.
, p. 81 - 86 (2007/10/02)
Up till now all attempts to synthesize organic thiazyl compounds in substance failed.Stabilization leads to the corresponding disulfide 2, the thioaminyl radical 7 and the sulphur diimide 8.Formally thiazyl compounds 1 and sulfenyl nitrenes 1 were resonance structures.Via sulfenyl nitrenes 1 the formation of 2, 7, 8 can be discussed.An in situ preparation of sulfenyl nitrene 1a via the sulfenyl chloride 5a, synthesized by chlorination of the disulfide 2a, and the sulfenyl azide 6a is described in detail. 1a can also be prepared from the sulfenyl amide 4a by oxidation.The structures of the radicals 7a-f and 12f are discussed.
DISULFIDES BY REDUCTION OF THIOSULFONIC S-ESTERS
Palumbo, Giovanni,Parrilli, Michelangelo,Neri, Orsola,Ferreri, Carla,Caputo, Romualdo
, p. 2391 - 2394 (2007/10/02)
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.
Chemistry of Sulfenic Acids. 3. Studies of Sterically Hindered Sulfenic Acids Using Flash Vacuum Pyrolysis
Davis, Franklin A.,Jenkins, Robert H.,Rizvi, Syed Q. A.,Yocklovich, Steven G.
, p. 3467 - 3474 (2007/10/02)
Flash vacuum pyrolysis (FVP) of sulfoxides containing β-hydrogen atoms affords sulfenic acids (RSOH) in good concentration under conditions where they are stable.The application of this technique to the synthesis and study of sterically hindered sulfenic acids 12a-e is described.The principal or primary reaction of simple sulfenic acids prepared in this manner is dehydration to thiosulfinates 13 (eq 1).Steric inhibition to dehydration (eq 1) appears to only be of importance for 2-methyl-2-propanesulfenic acid (12a) which was trapped in good yield with methyl propiolate to afford 16a. 2,4,6-Tri-tert-butylbenzenesulfenic acid (12e) appears to be destabilized as a consequence of interaction between the SOH and adjacent tert-butyl groups.In the pyrolysis section of the apparatus, 12e decomposes to phenol 21 and aryl radical 22, which reacts further.Thermolysis of sulfoxides generates the sulfenic acids 12a-e in very low concentration at any one time.The products of sulfenic acids generated in this way result from secondary reactions of the corresponding thiosulfinates.
Sulphone Formation from 2,4,6-Tri-isopropylbenzenesulphinic Acid
Adlington, Robert M.,Barrett, Anthony G. M.
, p. 1076 - 1079 (2007/10/02)
2,4,6-Tri-isopropylbenzenesulphinic acid decomposed in the presence of oxygen giving 2,4,6-tri-isopropyl-1,α-sultone; a mechanism involving arylsulphonyl and peroxyarylsulphonyl radicals and intramolecular hydrogen atom abstraction is suggested.
