16851-72-2

Usage

Uses

Used in Organic Synthesis:
N-(p-toluenesulfonyl)-3-pyrroline is used as a protecting group for amine and alcohol functional groups in organic synthesis reactions. The tosyl group can be easily removed under mild conditions to reveal the original functional group, making it a valuable tool in the synthesis of complex organic molecules.
Used in Pharmaceutical Synthesis:
N-(p-toluenesulfonyl)-3-pyrroline can be used as a building block in the synthesis of pharmaceuticals. Its ability to protect functional groups during organic reactions allows for the creation of more complex and effective drug molecules.
Used in Materials Science:
N-(p-toluenesulfonyl)-3-pyrroline may have applications in materials science, potentially contributing to the development of new materials with unique properties.
Used in Chemical Research:
As a member of the tosyl compounds class, N-(p-toluenesulfonyl)-3-pyrroline can be utilized in chemical research to explore new reaction pathways, mechanisms, and the development of novel synthetic methods.

InChI:InChI=1/C11H13NO2S/c1-10-4-6-11(7-5-10)15(13,14)12-8-2-3-9-12/h2-7H,8-9H2,1H3

Upstream product

• 1476-11-5 Z-1,4-dichlorobutene 
• 70-55-3 toluene-4-sulfonamide 
• 50487-72-4 N,N-Diallyltosylamide 
• 109-96-6 3-Pyrroline 
• 98-59-9 p-toluenesulfonyl chloride 
• 317842-50-5 4-methyl-N-(2-oxoethyl)-N-(prop-2-yn-1-yl)benzenesulfonamide 
• 1112-67-0 tetrabutyl-ammonium chloride 
• 126690-80-0 N-(p-toluenesulfonyl)-2-vinylaziridine 
• 764-41-0 1,4-dichloro-2-butene 
• 1174901-29-1 4-methyl-N-(buta-2,3-dienyl)-N-(2-(trimethylsilyl)buta-2,3-dienyl)benzenesulfonamide 
• 918871-59-7 C₁₄H₁₈O₂S 
• 1440956-52-4 1-tosylpyrrolidin-3-ylboronic acid 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 1440956-22-8 C₁₇H₂₆BNO₄S 

Downstream Products

• 6435-78-5 N-tosylpyrrolidine 
• 16851-78-8 3,4-dibromo-1-[(4-methylphenyl)sulfonyl]pyrrolidine 
• 170456-84-5 4-bromo-1-(toluene-4-sulfonyl)pyrrolidin-3-ol 
• 1018476-72-6 ((CH₃)4C₅H)Co(NO)2C₄H₆NSO₂C₆H₄CH₃ 
• 1004764-08-2 2-[4-(3-chloropropoxy)phenyl]-5-[(4-methylphenyl)sulfonyl]-4,5,6,6a-tetrahydro-3aH-pyrrolo[3,4-d][1,3]thiazol-3a-ol 
• 1004764-09-3 2-[4-(3-chloropropoxy)phenyl]-5-[(4-methylphenyl)sulfonyl]-5,6-dihydro-4H-pyrrolo[3,4-d][1,3]thiazole 
• 165883-19-2 (+)-(R)-3-phenyl-N-(p-toluenesulfonyl)pyrrolidine 

Relevant academic research and scientific papers

η6-mesityl,η1-imidazolinylidene-carbene- ruthenium(II) complexes: Catalytic activity of their allenylidene derivatives in alkene metathesis and cycloisomerisation reactions

The reaction of electron-rich carbene-precursor olefins containing two imidazolinylidene moieties [(2,4,6- Me3C6H2CH2)NCH2 CH2N(R)C=]2 (2a: R = CH2CH2OMe, 2

Carbon-carbon bond forming reactions with substrates absorbed non-covalently on a cellulose chromatography paper support

Reactions and purifications, including carbon-carbon bond forming reactions, can be carried out on a cellulose support on which the substrates are non-covalently absorbed. The Royal Society of Chemistry.

Organic-inorganic hybrid silica material derived from a monosilylated Grubbs-Hoveyda ruthenium carbene as a recyclable metathesis catalyst

The synthesis of a monosilylated Grubbs-Hoveyda ruthenium alkylidene complex is described, as well as the preparation and characterization of the corresponding material by sol-gel cogelification with tetraethoxysilane (TEOS) and the assay of this recyclab

Olefin metathesis in supercritical carbon dioxide

Liquid or supercritical carbon dioxide (scCO2) is a versatile reaction medium for ring-opening metathesis polymerization (ROMP) and ring-closing olefin metathesis (RCM) reactions using well-defined metal catalysts. The molybdenum alkylidene complex 1 and ruthenium carbenes 2 and 3 bearing PCy3 or N-heterocyclic carbene ligands, respectively, can be used and are found to exhibit efficiency similar to that in chlorinated organic solvents. While compound 1 is readily soluble in scCO2, complexes 2 and 3 behave like heterogeneous catalysts in this reaction medium. Importantly, however, the unique properties of scCO2 provide significant advantages beyond simple solvent replacement. This pertains to highly convenient workup procedures both for polymeric and low molecular weight products, to catalyst immobilization, to reaction tuning by density control (RCM versus acyclic diene metathesis polymerization), and to applications of scCO2 as a protective medium for basic amine functions. The latter phenomenon is explained by the reversible formation of the corresponding carbamic acid as evidenced by 1H NMR data obtained in compressed CO2. Together with its environmentally and toxicologically benign character, these unique physicochemical features sum up to a very attractive solvent profile of carbon dioxide for sustainable synthesis and production.

Immobilization of grubbs catalyst as supported ionic liquid catalyst (Ru-SILC)

Grubbs olefin metathesis catalyst was immobilized as a ruthenium-supported ionic liquid catalyst (Ru-SILC) in pores of amorphous alumina with the aid of ionic liquid [hmim]PF6. This Ru-SILC was effective for various olefin metathesis reactions

Occlusion of Grubbs' catalysts in active membranes of polydimethylsiloxane: Catalysis in water and new functional group selectivities

The Grubbs' first and second generation catalysts were occluded into cross-linked slabs of polydimethylsiloxane with volumes from 1 mm3 to 1 cm3 by swelling the polymer with catalyst and methylene chloride. Methylene chloride was evaporated under vacuum to yield occluded catalysts where their solvent was polydimethylsiloxane. These occluded catalysts were reacted with alkenes dissolved in H2O or H2O/MeOH mixtures that diffused into the polydimethylsiloxane to react by ring-closing metathesis and cross metathesis. Control experiments revealed that the catalysts remained occluded and metathesis did not occur in the solvent. Occlusion of these catalysts allowed commercially available Grubbs' catalysts to be used with H2O as the solvent while isolating the H2O sensitive ruthenium methylidene from exposure to H2O. Functional group selective experiments were carried out where the polydimethylsiloxane was an "active" membrane to exclude salts. Polydimethylsiloxane is a hydrophobic polymer, so the deprotonated salt of diallylmalonic acid did not diffuse into it while a diallylether diffused into it and reacted by metathesis. Thus, by controlling the polarity of reagents their reactivity can be controlled owing to the properties of polydimethylsiloxane rather than those of the Grubbs' catalysts. Occlusion of catalysts in polydimethylsiloxane has been shown to add new selectivities to mature catalysts. Copyright

Olefin metathesis catalyst bearing a chelating phosphine ligand

An improved synthetic procedure for the complex (SPY-5-34)-dichloro- (κ2(C,P)-diphenyl-(2-benzylidene)-phosphine)-(1,3-bis(2,4, 6-trimethylphenyl)-4,5-dihydro-imidazol-2-ylidene)-ruthenium (2) was elaborated and the title compound was tested as

Metathesis in pure water mediated by supramolecular additives

Supramolecular, water-soluble additives based on calix[n] arenes exhibit a beneficial influence on the ring-closing and cross metathesis of non-polar substrates in pure aqueous medium using standard Grubbs-II and Hoveyda-II catalysts. The catalytic activi

Mixed N-heterocyclic carbene/phosphite ruthenium complexes: Towards a new generation of olefin metathesis catalysts

The synthesis, characterisation and catalytic behaviour of ruthenium indenylidene complexes bearing an N-heterocyclic carbene and triisopropylphosphite are described.

An unusual cationic Ru(ii) indenylidene complex and its Ru(iii) derivative - Efficient catalysts for high temperature olefin metathesis reactions

The use of a mixed phosphite/N-heterocyclic carbene bearing ruthenium precursor permits the synthesis and characterisation of unprecedented four-coordinate Ru(ii) and Ru(iii) cationic complexes adopting an unusual sawhorse structure. The cationic Ru(ii) c