Category: 5034-06-0

Wang, Dengjin published the artcileOne-Carbon Chain Extension of Esters to α-Chloroketones: A Safer Route without Diazomethane, Name: trimethyloxosulphonium chloride, the publication is Journal of Organic Chemistry (2004), 69(5), 1629-1633, database is CAplus and MEDLINE.

The reaction of a variety of Me esters with dimethylsulfoxonium methylide at 0-25 °C affords the chain-extended β-keto dimethylsulfoxonium ylides. Subsequent treatment with hydrogen chloride in THF proceeds with loss of DMSO to afford the corresponding α-chloro ketones. This sequence has been utilized to convert the Me esters of CBZ-protected alanine and valine to the anti N-protected α-amino epoxides, which are important pharmaceutical intermediates. When the same protocol is applied to BOC-protected phenylalanine Me ester, epimerization occurs so that the use of a more reactive aryl ester is required. This chem. provides a practical route to α-chloroketones that avoids the use of toxic and explosive diazomethane.

Journal of Organic Chemistry published new progress about 5034-06-0. 5034-06-0 belongs to chlorides-buliding-blocks, auxiliary class Salt,Aliphatic hydrocarbon chain, name is trimethyloxosulphonium chloride, and the molecular formula is C11H14O2, Name: trimethyloxosulphonium chloride.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Honda, Mitsunori published the artcileSynthesis of 1-hydrocarbon substituted cyclopropyl silyl ketones, Safety of trimethyloxosulphonium chloride, the publication is Tetrahedron Letters (2018), 59(42), 3777-3781, database is CAplus.

The synthesis of cyclopropyl silyl ketones possessing a hydrocarbon group at 1-position of three-membered ring was investigated. The reaction of sulfoxonium ylide with α,β-unsaturated acylsilanes derived from α,β-unsaturated aldehydes did not afford the desired acylsilane derivatives Instead, the corresponding silyl enol ethers were yielded exclusively. On the other hand, the Corey-Chaykovsky cyclopropanation of α-substituted α,β-unsaturated aldehydes proceeded well to give 1-substituted cyclopropyl aldehydes. The silyl substitution of formyl proton in the obtained aldehydes via umpolung of carbonyl group afforded the target acylsilanes.

Tetrahedron Letters published new progress about 5034-06-0. 5034-06-0 belongs to chlorides-buliding-blocks, auxiliary class Salt,Aliphatic hydrocarbon chain, name is trimethyloxosulphonium chloride, and the molecular formula is C3H9ClOS, Safety of trimethyloxosulphonium chloride.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Busch, Brett B. published the artcileThe Boron-Catalyzed Polymerization of Dimethylsulfoxonium Methylide. A Living Polymethylene Synthesis, Computed Properties of 5034-06-0, the publication is Journal of the American Chemical Society (2002), 124(14), 3636-3646, database is CAplus and MEDLINE.

Trialkyl and aryl organoboranes catalyze the polymerization of dimethylsulfoxonium methylide (1). The product of the polymerization is a tris-polymethylene organoborane. Oxidation affords linear telechelic α-hydroxy polymethylene. The polymer mol. weight was found to be directly proportional to the stoichiometric ratio of ylide/borane, and polydispersities as low as 1.01-1.03 have been realized. Although oligomeric polymethylene has been the most frequent synthetic target of this method, polymeric star organoboranes with mol. weights of 1.5 million have been produced. The average turnover frequency at 120° in 1,2,4,5-tetrachlorobenzene/toluene is estimated at >6 × 10⁶ g of polymethylene (mol boron)^-1 h^-1. The mechanism of the polyhomologation reaction involves initial formation of a zwitterionic organoborane-ylide complex which breaks down in a rate-limiting 1,2-alkyl group migration with concomitant expulsion of a mol. of DMSO. The reaction was found to be first order in the borane catalyst and zero order in ylide. DMSO does not interfere with the reaction. The temperature dependence of the reaction rate yielded the following activation energy parameters (toluene, ΔH^⧧ = 23.2 kcal/mol, ΔS^⧧ = 12.6 cal deg/mol, ΔG^⧧ = 19.5 kcal/mol; THF, ΔH^⧧ = 26.5 kcal/mol, ΔS^⧧ = 21.5 cal deg/mol, ΔG^⧧ = 20.1 kcal/mol).

Journal of the American Chemical Society published new progress about 5034-06-0. 5034-06-0 belongs to chlorides-buliding-blocks, auxiliary class Salt,Aliphatic hydrocarbon chain, name is trimethyloxosulphonium chloride, and the molecular formula is C3H9ClOS, Computed Properties of 5034-06-0.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Wang, Dengjin published the artcileSynthesis of an anti-α-amino epoxide by one-carbon homologation of an α-amino ester: (2S,3S)-1,2-epoxy-3-(Boc-amino)-4-phenylbutane, SDS of cas: 5034-06-0, the publication is Organic Syntheses (2007), 58-67, database is CAplus.

The title compound was prepared by homologation of (S)-PhCH₂CH(NHBoc)CO₂C₆H₄NO₂-4 with Me₂S(O):CH₂, conversion to (S)-PhCH₂CH(NHBoc)CO₂CH₂Cl with HCl, and cyclization with LiAlH(OCMe₃)₃. Several other chloro ketones were also prepared

Organic Syntheses published new progress about 5034-06-0. 5034-06-0 belongs to chlorides-buliding-blocks, auxiliary class Salt,Aliphatic hydrocarbon chain, name is trimethyloxosulphonium chloride, and the molecular formula is C25H47NO8, SDS of cas: 5034-06-0.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Mangion, Ian K. published the artcileIridium-Catalyzed X-H Insertions of Sulfoxonium Ylides, Computed Properties of 5034-06-0, the publication is Organic Letters (2009), 11(16), 3566-3569, database is CAplus and MEDLINE.

The unique reactivity of sulfoxonium ylides as a carbene source is described for a variety of X-H bond insertions, taking advantage of a simple, com. available iridium catalyst. This method has applications in both intra- and intermol. reactivity, including a practical ring-expansion strategy for lactams. The safety and stability of sulfoxonium ylides recommend them as preferable surrogates to traditional diazo ketones and esters.

Organic Letters published new progress about 5034-06-0. 5034-06-0 belongs to chlorides-buliding-blocks, auxiliary class Salt,Aliphatic hydrocarbon chain, name is trimethyloxosulphonium chloride, and the molecular formula is C3H9ClOS, Computed Properties of 5034-06-0.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Koolpe, Gary A. published the artcileDiastereomeric 6-desoxy-6-spiro-α-methylene-γ-butyrolactone derivatives of naltrexone and oxymorphone. Selective irreversible inhibition of naltrexone binding in an opioid receptor preparation by a conformationally restricted Michael acceptor ligand, Quality Control of 5034-06-0, the publication is Journal of Medicinal Chemistry (1984), 27(12), 1718-23, database is CAplus and MEDLINE.

The title compounds I and II (R = Me or cyclopropylmethyl) were prepared by sequence reaction starting with direct alkylation of the diacetate ester of the parent ketone by the Reformatskii reagent prepared from Me α–(bromomethyl)acrylate  [4224-69-5], and their affinity for opioid binding sites was determined in crude rat brain membrane preparation by competition against [³H]naltrexone in presence and absence of Na⁺. 6α–(2-Carboxyallyl)-17-(cyclopropylmethyl)-4,5α-epoxy-3,6β,14-trihydroxymorphinan-γ-lactone (II; R = cyclopropylmethyl) [92398-30-6] was the most potent compound showing a 50% inhibition of binding at 5 nM. The data suggest a receptor nucleophile such as SH is located where it can add to the α,β-unsaturated carbonyl system of the above compound

Journal of Medicinal Chemistry published new progress about 5034-06-0. 5034-06-0 belongs to chlorides-buliding-blocks, auxiliary class Salt,Aliphatic hydrocarbon chain, name is trimethyloxosulphonium chloride, and the molecular formula is C3H9ClOS, Quality Control of 5034-06-0.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Onuki, Yuta published the artcileRing-opening cyclization of spirocyclopropanes using sulfoxonium ylides, Safety of trimethyloxosulphonium chloride, the publication is Chemical & Pharmaceutical Bulletin (2020), 68(5), 479-486, database is CAplus and MEDLINE.

Ring-opening cyclization of cyclohexane-1,3-dione-2-spirocyclopropanes I (R = H, Me, Ph; R¹ = H, Me; R² = H, Ph, 4-methylphenyl, 4-bromophenyl, n-butyl; n = 1) using dimethylsulfoxonium methylide proceeded regioselectively to produce 2,3,4,6,7,8-hexahydro-5H-1-benzopyran-5-ones II (R³ = H; n = 1) in good to high yields. The reactions of cycloheptane- and cyclopentane-1,3-dione-2-spirocyclopropanes I (R = H; R¹ = H; R² = phenyl; n = 0 or 2) could construct [7.6]- and [5.6]-fused ring systems II (R³ = H; n = 0 or 2). This reaction was also carried out using triethyl(oxo)-sulfanylium chloride, tributyl(oxo)-sulfanylium chloride, and benzyldimethyloxo-sulfanylium chloride, resulting in the formation of the corresponding 2,3-trans-disubstituted products III (R⁴ = Ph; R⁵ = Me, Pr, phenyl) and II (R = H; R¹ = H; R² = H; R³ = Ph; n = 1) in good to high yields, and it was shown that the di-Me group can act as a dummy substituent. It was found that the 2- and 3-phenyhexahydrobenzopyran-5-ones II (R = H; R¹ = H; R² = H, phenyl; n = 1) can be readily converted into 5-hydroxyflavan and 5-hydroxyisoflavan, resp.

Chemical & Pharmaceutical Bulletin published new progress about 5034-06-0. 5034-06-0 belongs to chlorides-buliding-blocks, auxiliary class Salt,Aliphatic hydrocarbon chain, name is trimethyloxosulphonium chloride, and the molecular formula is C3H9ClOS, Safety of trimethyloxosulphonium chloride.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Kawanishi, Hiroyuki published the artcileStereoselective synthesis of antifungal sulfoximines, novel triazoles II, Safety of trimethyloxosulphonium chloride, the publication is Heterocycles (1998), 181-190, database is CAplus.

Novel triazole derivatives I (R = H, MeCO, MeNHCO, Me, MeO₂CCH₂) with an N-substituted sulfoximine moiety were synthesized and evaluated for antifungal activity. These compounds showed significantly weaker activity than I (R = H); the N-H moiety of the sulfoximine was extremely important for the activity. A practical and effective stereoselective synthesis of (-)-I (R = H), considered to be the most promising antifungal compound, has been developed. (-)-I (R = H) is prepared in seven steps, including two resolution steps, from the methylthiodifluoropropiophenone II, by epoxidation with Me₃SO⁺ Cl^–, diastereoselective sulfimine formation with chloramine T, addition of 1,2,4-triazole to the epoxide, oxidation of the sulfimine, acid hydrolysis of toluenesulfonyl group of the sulfoximine, and resolution with the novel resolving agent 1-(2,3,4-trichlorophenyl)ethanesulfonic acid [(+)-TCPES] III.

Heterocycles published new progress about 5034-06-0. 5034-06-0 belongs to chlorides-buliding-blocks, auxiliary class Salt,Aliphatic hydrocarbon chain, name is trimethyloxosulphonium chloride, and the molecular formula is C3H9ClOS, Safety of trimethyloxosulphonium chloride.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Chen, Guanghui published the artcileSynthesis of Functional Olefin Copolymers with Controllable Topologies Using a Chain-Walking Catalyst, Name: trimethyloxosulphonium chloride, the publication is Journal of the American Chemical Society (2003), 125(22), 6697-6704, database is CAplus and MEDLINE.

The branching topol. of ethylene polar copolymers was for the first time successfully controlled by copolymerization of ethylene with polar olefins using a palladium-bisimine chain-walking catalyst, in which ethylene pressure and comonomer concentration were used to control the competition between isomerization (chain-walking) and monomer insertion processes. Although the overall branching d. changes slightly, the topol. of the copolymers becomes more dendritic as the ethylene pressure and comonomer feed concentration are decreasing. This provides a straightforward one-pot synthesis to access a full range of functional copolymers having controllable branching topologies. To demonstrate the utility of this methodol., dendritic functional copolymers having hydroxyl, epoxide, and carbohydrate groups were prepared in a one-pot polymerization as potential functional materials.

Journal of the American Chemical Society published new progress about 5034-06-0. 5034-06-0 belongs to chlorides-buliding-blocks, auxiliary class Salt,Aliphatic hydrocarbon chain, name is trimethyloxosulphonium chloride, and the molecular formula is C3H9ClOS, Name: trimethyloxosulphonium chloride.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Luo, Jun published the artcileHydrocarbon Waxes from a Salt in Water: The C1 Polymerization of Trimethylsulfoxonium Halide, Safety of trimethyloxosulphonium chloride, the publication is ACS Macro Letters (2012), 1(5), 560-563, database is CAplus and MEDLINE.

We report the synthesis of polymethylene waxes, a surrogate of PE waxes, by a controlled polymerization reaction in water at or near r.t. and under atm. pressure. The monomer, dimethylsulfoxonium methylide, is generated in situ from a salt, trimethylsulfoxonium halide. The carbon sources for the polymerizations are C1 mols., which can be derived from nonpetroleum feedstock. DMSO serves as the C1 carrier and is not consumed. The reaction is initiated and catalyzed by trialkylboranes, compounds that are stable in water. A certain degree of mol. weight control is achieved by adjusting the stoichiometry of “salt” to organoborane. Polymethylene, the simplest hydrocarbon polymer, is a semicrystalline material. The room temperature polymerization produces a linear polymer approx. 100°C below its melting temperature (T_m). The supercooled polymers rapidly crystallize into flat nanoparticles comprised of stacked lamellae.

ACS Macro Letters published new progress about 5034-06-0. 5034-06-0 belongs to chlorides-buliding-blocks, auxiliary class Salt,Aliphatic hydrocarbon chain, name is trimethyloxosulphonium chloride, and the molecular formula is C3H9ClOS, Safety of trimethyloxosulphonium chloride.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics