4058-26-8Relevant articles and documents
Styrylsulfonates and -Sulfonamides through Pd-Catalysed Matsuda–Heck Reactions of Vinylsulfonic Acid Derivatives and Arenediazonium Salts
Schmidt, Bernd,Wolf, Felix,Brunner, Heiko
supporting information, p. 2972 - 2982 (2016/07/11)
Arene diazonium salts undergo Matsuda–Heck reactions with vinylsulfonates and -sulfonamides to give styrylsulfonic acid derivatives in high to excellent yields and with high to excellent selectivities. By quantifying the evolution of nitrogen over time in a gas-meter apparatus, the reactivities of ethylvinylsulfonate and the benchmark olefin methyl acrylate were compared for an electron-rich and an -deficient arene diazonium salt. Tertiary sulfonamides react in Matsuda–Heck couplings with high conversions, but require long reaction times, which prevents the determination of kinetic data through the measurement of nitrogen evolution. Secondary sulfonamides were found to be unreactive. From these results, the following order of reactivity could be deduced: H2C=CHCO2Me > H2C=CHSO2OEt > H2C=CHSO2N(Me)Bn >> H2C=CHSO2NHBn. Through the Matsuda–Heck coupling of 5-indolyldiazonium salt and a tertiary vinylsulfonamide, the synthesis of the C-5-substituted indole part of the antimigraine drug naratriptan was accomplished in high yield.
Using the same and a silane compound or multiple single molecular composition for forming molecular layer
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Paragraph 0033; 0034, (2016/10/17)
[Problem] To provide a novel silane compound and a composition for formation of a monolayer or a multilayer on a substrate. [Solution] A composition for formation of a monolayer or a multilayer containing a silane compound represented by formula (1A) or formula (1B), and an organic solvent. [Chem 1] [In the formulae, each R1 independently represents a methyl group or an ethyl group, each X independently represents a C1-10 linking group, Z represents a phthalic imide group, a maleimide group, or a succinic imide group which may have at least one substituent, each Ar independently represents a phenyl group or a naphthyl group, and the linking group represented by X may contain at least one oxygen atom or sulfur atom in the main chain, and when the Ar is a phenyl group, the phenyl group may have at least one substituent.]
Controlled synthesis of sulfonated block copolymers having thermoresponsive property by RAFT polymerization of vinyl sulfonate esters
Mori, Hideharu,Saito, Yosuke,Takahashi, Eri,Nakabayashi, Kazuhiro,Onuma, Atsuhiko,Morishima, Makoto
experimental part, p. 3861 - 3877 (2012/10/18)
Four vinyl sulfonate ester derivatives, methyl ethenesulfonate (MES), ethyl ethenesulfonate (EES), 2,2,2-trifluoroethyl ethenesulfonate (TFES), and 2,2,2-trichloroethyl ethenesulfonate (TCLES), which are protected forms of vinyl sulfonic acids, were polymerized by reversible addition-fragmentation chain transfer (RAFT) polymerization. Polymers having relatively narrow molecular weight distributions and pre-determined molecular weights were obtained by the polymerization of all monomers using a suitable xanthate-type chain transfer agent (CTA). The RAFT polymerizations of EES and TCLES were found to proceed in controlled fashions under suitable conditions, as confirmed by the formation of narrow polydispersity products, molecular weights controlled by the monomer/chain transfer agent ratio, and linear increases in molecular weight with conversion. Deprotection of the ethyl group of poly(EES) by LiBr in refluxing 2-butanone proceeded smoothly to give water-soluble poly(lithium vinyl sulfonate). Poly(potassium vinyl sulfonate) was also obtained by the deprotection of poly(TCLES) using potassium tert-butoxide. The syntheses of thermoresponsive block copolymers involving poly(lithium vinyl sulfonate) segments were conducted by RAFT polymerization of N-isopropylacrylamide using poly(EES) macro-CTA, followed by deprotection. The thermally-induced phase separation behavior and assembled structures of the block copolymers were also studied in aqueous solution.
Dioxygen mediated hydroacylation of vinyl sulfonates and sulfones on water
Chudasama, Vijay,Fitzmaurice, Richard J.,Ahern, Jenna M.,Caddick, Stephen
supporting information; experimental part, p. 133 - 135 (2010/04/01)
Herein we report a mild, facile method for the preparation of 1,4-keto-sulfonates and sulfones on water. Further synthetic manipulations can result in products that are not readily accessed by hydroacylation of electron rich alkenes.
Design and synthesis of a bifunctional label for selection of β-lactamase displayed on filamentous bacteriophage by catalytic activity
Marchand-Brynaert, Jacqueline,Bouchet, Michele,Touillaux, Roland,Beauve, Cecile,Fastrez, Jacques
, p. 5591 - 5606 (2007/10/03)
A bifunctional activity label 1c has been constructed for the selection of active β-lactamases displayed on filamentous bacteriophage. It features an original 6-sulfonylamido-penam sulfone moiety, as β-lactamase suicide-inhibitor, and a biotinyl residue, for separation by affinity chromatography, connected through a linker including a cleavable disulfide bond. The inhibitor 28 resulted from coupling of methoxymethyl 6-aminopenicillinate 8 with N-protected (aminoethoxy)ethoxyethanesulfonyl chloride 23, followed by oxidation into the corresponding sulfone 25, and usual deprotections. The biotinyl ester 32 reacted with 3-(2-aminoethyldithio)propanoic acid 31 as linker, to give 33 which was further activated as pentafluorophenol ester 34b. Final coupling of the building blocks 28 and 34b gave the target label 1c.
