MT-sulfone

Alternate Names MT-sulfone formaldehyde methyl />-tolyl dithioacetal 5, 5-dioxide methyl />-toluenesulfonyhnethyl sulfide methylthio(/>-toluenesulfonyl)methane. 

Synthesis of Esters and Aldehydes. Monoalkylation of methylthiomethyl p-tolyl sulfone (MT-sulfone) with an alkyl halide is achieved by the action of a phase-transfer catalyst (PTC) in toluene-50% aq NaOH. sodium hydride and butyl-lithium also generate a carbanion of MT-sulfone. Arylmethyl derivatives of MT-sulfone are prepared by sodium borohydride reduction of the Knoevenagel condensation products with aromatic aldehydes. The monoalkylated products are converted into the corresponding methyl esters (eq 1). This functionalization can be utilized for synthesizing a-alkoxy carboxylic esters (eq 2) and Q -amino acids (eq 3). ... 

The carbanion of MT-sulfone is stable enough to add to a,/3-unsaturated carbonyl compounds in a [1,4] fashion. The... 

Ketone Synthesis. The monoalkylated MT-sulfone undergoes further alkylation by action of alkyl halide and NaH or n-BuLi to give a dialkylated product. Since the dialkylated product can be hydrolyzed easily, MT-sulfone has proven to be very useful for synthesizing ketones (eq 5). Symmetrical ketones are prepared by direct dialkylation with NaH and alkyl hahde in DMF and hydrolysis (eq 6). Cyclic ketones are also synthesized from a,a>-dihaloalkanes. An efficient synthesis of a-hydroxy ketones is also achieved by the addition of the monoalkyl derivative to an aldehyde to give an adduct and subsequent hydrolysis (eq 7). ... 

Acylation of MT-sulfone. MT-sulfone was acylated by treatment with an ester and excess NaH in THF. The acylated MT-sulfone was oxidized with hydrogen peroxide in acetic acid, by slowly warming the reaction to give an 5-methyl a-keto car-bothioate (eq 8). ... 

An alkoxyacetyl derivative of MT-sulfone exhibits intriguing behavior on treatment with a weak base to form an acetal of 3-methylthio-2-oxopropanal (eq 9). ... 

Synthesis of a,jS-Unsaturated Ketones. Alkylidene derivatives of MT-sulfone are useful synthetic precursors for a,/3-un-saturated ketones (eq 10). This method can be extended to provide an efficient synthesis of a,/3,y,5-unsaturated aldehydes and ketones (eq 11). ... 

Methyl Methylthiomethyl Sulfone. Methyl methyl-thiomethyl sulfone is the 5-methyl analog of MT-sulfone and it is conveniently synthesized by oxidation of methyl methylthiomethyl sulfoxide (FAMSO) with potassium permanganate or H202-Na0H. It is useful for synthetic methods similar to those using MT-sulfone synthesis of carboxylic esters, ketones, and a-aLkoxy- -arylacetates. In the reaction of this reagent with allylic bromides, a-methylthio- /,5-unsaturated sulfones are obtained by stirring the bromide with potassium carbonate and potassium iodide in hexamethylphosphoric triamide (eq 14), which does not occur with MT-sulfone. 

In soft cheeses, such as Brie, Camembert, and Limburger, the following sulfur compounds were implicated 3-(methylthio)propanol, MT, DMS, DMDS, DMTS, dimethyl tetrasulfide, methyl ethyl disulfide, diethyl disulfide, 2,4-dithiapentane, 3-methylthio-2,4-dithiapentane, methional, 2,4,5-trithiahex-ane, 1,1-fe-methylmercaptodisulfide, methyl thioacetate (=methanethiol acetate), benzothiazole, methylthiobenzothiazole, methyl ethyl sulfonate, methyl methane thiosulfonate, thiophene 2-aldehyde, and H2S.34 Many of these were only present in small amounts Limburger cheese was notable for 13.2% of DMDS, 0.5% of methyl thioacetate, and 0.8% of DMTS. 

The ee values of the sulfides 5aa and 5ba are significantly lower than those of the corresponding sulfones 2aa and 2ba. Kinetic resolution and substitution of the acyclic carbonates rac-3aa and roc-3ba with the thiol under the conditions used above proceeded with similar high selectivities and gave the carbonates ent-3aa and mt-3ba, respectively, and the sulfides 6aa and 6ba, respectively (entries 3 and 4). The reactions of the cyclic carbonates rac-laa and rac-lba went to 50%... 

For instance, methyl tert-butyl ether (MTBE) used worldwide as an octane improver in gasoline is produced at a still growing global capacity of approx. 8 million mt/yr using sulfonated resins as catalysts (ref. 1). 

The ESR spectra of the anion radicals 246 derived from a series of 4-dicyanom ethyl idene-4//-thiopy ran sulfones show clearly resolved hyperfine structure centred around g values of ca. 2000. Large nitrogen splitting of 1.0-1.5 mT and FI-3 and FI-5 splitting of 0.3-0.93 mT are observed <1995JOC1674>. 

Vinyl sulfones are useful building blocks for synthetic organic chemistry. Nucleophilic epoxida-tion of chiral (,S )-2-tosyl-2-cyclohexenol (1) and its 0-protected derivatives proceeds with excellent diastcrcosclcctivitics and good yields.. mt-Epoxides 2 of 98% optical purity are obtained, except for the silylated derivative which is much less selective when epoxidized with lithium tt-77-butylperoxide, and, similarly to the acetyl derivative, is incompatible with standard Weitz-Scheffer conditions68. 

Bose-O Reilly S, Drasch G, Beinhoee C, Maydl S, VosKO MR, Roider G and Dzaja D (2003) The Mt. Diwata Study on the Philippines 2000 -treatment of mercury intoxicated inhabitants of a gold mining area with DMPS (2,3-Dimercapto-l-propane-sulfonic acid, Dimaval ). Sci Total Environ 307 71-82. 

An extractant composed of the quaternary amine and dinonyl naphthalenesulfonic acid was chosen for further process development it is prepared by mixing the sulfonic acid with methyl tricaprylyl amine chloride [MT(OD)A, Aliquat-336 from Henkel, and washing with water to remove the HCl from the organic phase. This extractant shows sufficient capacity and good reversibility (see curve B in Fig. 17). An increase of the extractant concentration from 0.25 to 0.31 M and to 0.50 M increases the capacity proportionally. At the elevated temperature chosen for the process (about 80°C) the viscosity of the 0.50 M extractant is acceptable. Elevation of the temperature from 22 to 88°C has only a small effect on extraction efficiency. 

Aerosol OT-100% Methyl hydroxyethyl-cellulose Monawet MT-70E Nonoxynol-9 Tylose MH Grades Tylose MHB dispersant, suspension polymerizations Luviskol K17 Luviskol K30 Luviskol K60 Luviskol K90 dispersant, synthetic latex Sodium polynaphthalene sulfonate dispersant, synthetic polymers Daxad 11G... 

T012 Mazawet IT, MERPOL HCS Monawet MM-80 Monawet MT-70E NIaproof Anionic Surfactant 4 Nonoxynol-2 Nonoxynol-3, Nonoxynoi-5 Nonoxynol-7 Nonoxynol-8, Nonoxynoi-11 Nonoxynol-13 Nonoxynoi-15 Nonoxynoi-28, Nonoxynol-40, Nonoxynol-58, Nonoxynol-108, Octoxynol-3, Octoxynol-8, Octoxynoi-18, Octoxynol-IS Octoxynol-30 Oleoyl sarcosine PEG-15 cocamine, PEG-B cocoate PEG hydrogenated castor oil, PEG-30 tetramethyl decynedbl Pentex 99 Plurafac RA-40 Pluronlc L92 Polysorbate 28, Polysorbate 81 Rhodacal 330 Rhodafac RE-960 SECOSOL DOS 70 Sodium dinonyl sulfosuccinate Sodium dodecylbenzene-sulfonate Sodium myristyl sulfate. 

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