38764-58-8Relevant academic research and scientific papers
Copper-catalyzed imination of sulfoxides and sulfides
Liu, Yuanyuan,Wang, Hanying,Yang, Xianjin
supporting information, p. 4697 - 4702 (2019/07/22)
Sulfoximines and sulfilimines have attracted considerable interest among organic chemists. The Cu(II)-catalyzed imination of sulfoxides and sulfides using various N-fluoro benzenesulfonamides was investigated in this study. The scope of the reaction was demonstrated by using several substituted sulfides and sulfoxides. The flow strategy for the preparation of NH-sulfoximines was also examined. By trapping nitrene intermediates through triphenylphosphine, we found that the reaction was conducted through a metal-nitrene intermediate mechanism.
SuFEx Chemistry of Thionyl Tetrafluoride (SOF4) with Organolithium Nucleophiles: Synthesis of Sulfonimidoyl Fluorides, Sulfoximines, Sulfonimidamides, and Sulfonimidates
Gao, Bing,Li, Suhua,Wu, Peng,Moses, John E.,Sharpless, K. Barry
supporting information, p. 1939 - 1943 (2018/01/22)
Thionyl tetrafluoride (SOF4) is a valuable connective gas for sulfur fluoride exchange (SuFEx) click chemistry that enables multidimensional linkages to be created via sulfur–oxygen and sulfur–nitrogen bonds. Herein, we expand the available SuFEx chemistry of SOF4 to include organolithium nucleophiles, and demonstrate, for the first time, the controlled projection of sulfur–carbon links at the sulfur center of SOF4-derived iminosulfur oxydifluorides (R1?N=SOF2). This method provides rapid and modular access to sulfonimidoyl fluorides (R1?N=SOFR2), another array of versatile SuFEx connectors with readily tunable reactivity of the S?F handle. Divergent connections derived from these valuable sulfonimidoyl fluoride units are also demonstrated, including the synthesis of sulfoximines, sulfonimidamides, and sulfonimidates.
A versatile and highly reactive polyfluorinated hypervalent iodine (III) compound
Schaefer, Sascha,Wirth, Thomas
supporting information; experimental part, p. 2786 - 2789 (2010/07/06)
(Figure Presented) Hyper-reactive: A highly reactive, fully fluorinated hypervalent iodine reagent (see formula) mediates new transformations (e.g. the one-pot conversion of sulfides to sulfoximines) and serves as a stoichiometric oxidant in well-established reactions (e.g. C-C bond cleavage and the conversion of alcohols into aldehydes).
Synthesis of diarylsulfoximines by the Friedel-Crafts reaction of sulfonimidoyl chlorides
Furusho,Okada,Takata
, p. 2827 - 2828 (2007/10/03)
In the presence of an equimolar amount of FeCl3, sulfonimidoyl chlorides were allowed to react with aromatic compounds to give the corresponding sulfoximines. Structure of the sulfonimidoyl chlorides and the aromatic compounds had considerable
Facile conversion of sulfilimines into sulfoximines using dioxiranes
Gaggero, Nicoletta,D'Accolti, Lucia,Colonna, Stefano,Curci, Ruggero
, p. 5559 - 5562 (2007/10/03)
Employing dimethyldioxirane, the direct conversion of several N-(p-tolylsulfonyl)sulfilimines and of one N-(acetyl)sulfilimine into the corresponding sulfoximines was achieved in high yield under mild conditions. Optically active S-(p-tolyl)-S-methyl-N-(p
Differences in the Course of Reactions of N,N-Dichloroamides of Carboxylic and Sulfonic Acids with Diaryl Sulfoxides
Pigin, O. V.,Krasnov, V. L.,Groshev, Yu. G.,Bel'skii, V. K.,Bodrikov, I. V.
, p. 1520 - 1525 (2007/10/03)
N,N-Dichloroamides of carboxylic acids are donors of oxygen in the reaction with diaryl sulfoxides that results in the formation of diaryl sulfones and the corresponding nitriles (oxidation of sulfoxides).N,N-Dichloroamides of sulfonic acids in the reaction with the same sulfoxides form N-arylsulfonyl-S,S-diarylsulfoxyimines (imination of sulfoxides).Based on the results of the MNDO calculations, probable intermediates responsible for realizing of a certain reaction pathway are suggested.
COPPER CATALYZED REACTIONS OF S,S-DIARYL-N-TOSYLSULFILIMINES WITH SULFOXIDES: NEW SYNTHESIS OF N-TOSYLSULFOXIMINES
Akutagawa, Kunihiko,Furukawa, Naomichi,Oae, Shigeru
, p. 213 - 222 (2007/10/02)
S,S-Diaryl-N-tosylsulfilimines were readily reduced by treatment with copper to give the corresponding sulfides and a copper-tosylnitrenoid-complex which upon reacting with sulfoxides afforded the corresponding N-tosylsulfoximines, derived from sulfoxides in fair yields.When optically active (-)-(S)-methylphenyl sulfoxide was used, the corresponding (+)-N-tosylsulfoximine was obtained together with the sulfide derived from the N-tosylsulfilimine.The stereochemical course of the conversion of (-)-(S)-sulfoxide to (+)-N-tosylsulfoximine was found to be mainly retention (76percent) with partial racemization due to thermal pyramidal inversion of the starting sulfoxide.
PREPARATION OF S,S-DIPHENYLSULFILIMINES, -SULFOXIMINES, AND -N-(P-TOLYLSULFONYL)SULFONEDIIMINES N-SUBSTITUTED WITH SULFUR GROUPS OF DIFFERENT OXIDATION STATES.
Akutagawa,Furukawa,Oae
, p. 518 - 524 (2007/10/02)
S,S-Diphenyl-N-(p-tolylthio)-, -N-(p-tolysulfinyl)-, -N-(p-toluenesulfinimidoyl-, -N-(p-tolsulfonyl)-, and -N-(p-toluenesulfonimidoyl)sulfoximines have been synthesized either by sulfenylation, sulfinylation, sulfinimidoylation, sulfonylation, and sulfoni
Oxidation of S,S-Diaryl-N-(p-tolylsulfonyl)sulfilimines and N-Unsubstituted S,S-Diaryl-sulfilimines with Potassium Hyperoxide Anion Radical (O2-.) in the Presence of 1-Bromopropane, Benzoyl Chloride, p-Tolylsulfonyl Chloride, Carbon Tetrachloride, Chloroform, or Dichloromethane in
Akutagawa, Kunihiko,Furukawa, Naomichi,Oae, Shigeru
, p. 1104 - 1107 (2007/10/02)
The reaction of S,S-diaryl-N-(p-tolylsulfonyl)sulfilimines and N-unsubstituted diaryl-sulfilimines with hydroperoxide anion radical (O2-.) in the presence of 18-crown-6 as a catalyst together with 1-bromopropane/benzene, benzoyl chloride/benzene, p-tolylsulfonyl chloride/benzene, carbon tetrachloride, chloroform, or dichloromethane, gave the corresponding sulfoximines, through nucleophilic oxidation with an intermadiary dioxy species formed upon treatment of organic halides with potassium hyperoxide (KO2).
