Novel Synthesis of N-Sulfonylsulfoximines and N-Sulfonylsulfilimines

Ohashi, Takeki; Matsunaga, Kazuo; Okahara, Mitsuo; Komori, Saburô

doi:10.1055/s-1971-21675

Cited by 11 publications

(5 citation statements)

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“…Electrochemical Imination of Sulfoxides. The nitrene transfer to sulfur was investigated similarly to aziridination . The redox behavior of sulfoxides on platinum was first studied using cyclic voltammetry (Figure ).…”

Section: Resultsmentioning

confidence: 99%

Development of Electrochemical Processes for Nitrene Generation and Transfer

2005

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An electrochemical strategy for running nitrogen-transfer reactions on chemically inert anode surfaces has been developed. The generation and trapping of highly reactive nitrene-transfer reagents can be accomplished under mild conditions on platinum electrodes. The key factor that accounts for the high levels of chemoselectivity in this process is the phenomenon of overpotential. We have found that molecules that are similar in terms of propensity toward oxidation can be differentiated on the basis of their affinity to a given electrode surface. Thereby, reactive species can be selectively generated in the presence of acceptor molecules of interest. Specifically, a wide range of structurally dissimilar olefins can be transformed into the corresponding aziridines in the presence of N-aminophthalimide. Likewise, nitrene generation in the presence of sulfoxides leads to their chemoselective transformation into the corresponding sulfoximines. In this paper we discuss the underlying mechanistic foundation of these reactions.

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Section: Resultsmentioning

confidence: 99%

Development of Electrochemical Processes for Nitrene Generation and Transfer

2005

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“…Famous examples are iminations involving TsN 3 77, 78 (Scheme 1, Path E) or various N-amino substituted compounds (Scheme 1, Path H). [85][86][87][88][89][90][91] An interesting application of this chemistry, going beyond its immediate importance as a source of (optically active) sulfoximines is a thermal fragmentation reaction yielding sterically congested alkenes (Scheme 3). 87…”

Section: From Sulfoxides and Sulfiliminesmentioning

confidence: 99%

Sulfoximines: Structures, Properties and Synthetic Applications

2000

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This review presents a comprehensive treatment of sulfoximine chemistry particularly emphasising synthetic developments and structural work after 1985. Following a brief introduction, the structures and properties of sulfoximines and metallated sulfoximines are discussed. The second section deals with the preparation of sulfoximines emphasising new methods. The main part of the review is concerned with reactions of sulfoximines. The material in this section is organised based on the reactivity pattern displayed by the various sulfoximines. Therefore they are grouped roughly into three classes of compounds. The first group of sulfoximines comprises compounds acting as C-nucleophiles, the second one contains electrophilic sulfoximines and the last group is made up of sulfoximines being useful as (chiral) ligands particularly for transition metals. Finally the ability of sulfoximines to act as "chiral chemical chameleons" and their rôle in biological and medicinal chemistry is briefly discussed.

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“…Since the discovery of the gelation of a mixture of xanthan-locust bean gum through a synergistic interaction [39] , many trials have been performed to find curves of 2% TSX with 0.1% EGCG (Scanning rate 0.5 ℃/min, Frequency 1 rad/s, NITTA et al [37] ) Fig.7 Temperature dependence of storage and loss elastic moduli of 20% corn starch gels stored at 5 ℃ for one (a) and seven (b) days (Frequency 3 Hz, strain 0.003 3, YOSHIMURA et al [38] ) other useful combinations of different polysaccharides or proteins which lead to the gelation. Gelation of mixtures of different biopolymers has been reported recently for gellan-xyloglucan [40−41] and gellan-hyaluronan [42] , where each individual biopolymer does not form a gel.…”

Section: Biopolymer Mixturesmentioning

confidence: 99%

Rheological and related studies on industrially important polysaccharides and proteins

Nishinari

2007

J Cent. South Univ. Technol.

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Gelation kinetics, mechanical spectra, thermal scanning rheology, and differential scanning calorimetry in aqueous solutions of gelling polymers and colloids such as starch, seaweed polysaccharides (agarose, carrageenans), microbial polysaccharides (gellan, curdlan), cellulose derivatives (methylcellulose), globular proteins, gelatin, and polyvinyl alcohol, which are used widely in foods, cosmetics, biomedical and pharmaceutical applications, are described. Some gelation processes at a constant temperature were treated by an equation of first order kinetics or by other modified equations, and the molecular mechanism of gel formation is discussed. Frequency and temperature dependences of gelling biopolymers are also described.

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Novel Synthesis of N-Sulfonylsulfoximines and N-Sulfonylsulfilimines

Cited by 11 publications

References 0 publications

Development of Electrochemical Processes for Nitrene Generation and Transfer

Development of Electrochemical Processes for Nitrene Generation and Transfer

Sulfoximines: Structures, Properties and Synthetic Applications

Rheological and related studies on industrially important polysaccharides and proteins

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