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Sulfides dimethyl

Katayama, S. Watanabe, T. Yamauchi, M., Chem. Pharm. Bull. 1992, 40, 2836. [Pg.144]

Solubility sol CH2CI2, ether, and THE, but CH2CI2 is the solvent of choice reacts rapidly with protic solvents.  [Pg.144]

Preparative Methods most conveniently prepared from commercially available monochloroborane-dimethyl sulfide complex and 2,3-dimethyl-2-butene in CH2CI2 (eq 1).  [Pg.144]

Analysis of Reagent Purity analyzed by B NMR and IR spectroscopy and by hydrogen evolution upon reaction with methanol.  [Pg.144]

Handling, Storage, and Precautions very reactive with oxygen and moisture and must be handled using standard techniques for handling air-sensitive materials. Reported to be stable for at least two months when stored at 0°C in CH2CI2 solution under N2.  [Pg.144]


The desired pyridylamine was obtained in 69 % overall yield by monomethylation of 2-(aminomethyl)pyridine following a literature procedure (Scheme 4.14). First amine 4.48 was converted into formamide 4.49, through reaction with the in situ prepared mixed anhydride of acetic acid and formic acid. Reduction of 4.49 with borane dimethyl sulfide complex produced diamine 4.50. This compound could be used successfully in the Mannich reaction with 4.39, affording crude 4.51 in 92 % yield (Scheme 4.15). Analogous to 4.44, 4.51 also coordinates to copper(II) in water, as indicated by a shift of the UV-absorption maximum from 296 nm to 308 nm. [Pg.116]

Pyridyl)hydrazine (Aldrich), 4-acetylpyridine (Acros), N,N,N -trimethylethylenediamine (Aldrich), methylrhenium trioxide (Aldrich), InQj (Aldrich), Cu(N0j)2-3H20 (Merck), Ni(N03)2-6Il20 (Merck), Yb(OTf)3(Fluka), Sc(OTf)3 (Fluka), 2-(aminomethyl)pyridine (Acros), benzylideneacetone (Aldrich), and chalcone (Aldrich) were of the highest purity available. Borane dimethyl sulfide (2M solution in THE) was obtained from Aldrich. Methyl vinyl ketone was distilled prior to use. Cyclopentadiene was prepared from its dimer immediately before use. (R)-l-acetyl-5-isopropoxy-3-pyrrolin-2-one (4.15) has been kindly provided by Prof H. Hiemstra (University of Amsterdam). [Pg.119]

Aldehydes are easily oxidized to carboxylic acids under conditions of ozonide hydroly SIS When one wishes to isolate the aldehyde itself a reducing agent such as zinc is included during the hydrolysis step Zinc reduces the ozonide and reacts with any oxi dants present (excess ozone and hydrogen peroxide) to prevent them from oxidizing any aldehyde formed An alternative more modem technique follows ozone treatment of the alkene m methanol with reduction by dimethyl sulfide (CH3SCH3)... [Pg.263]

Make a molecular model of dimethyl sulfide How does its bond angle at sulfur compare with the C—O—C bond angle in dimethyl ether"d... [Pg.700]

Diborane [19287-45-7] the first hydroborating agent studied, reacts sluggishly with olefins in the gas phase (14,15). In the presence of weak Lewis bases, eg, ethers and sulfides, it undergoes rapid reaction at room temperature or even below 0°C (16—18). The catalytic effect of these compounds on the hydroboration reaction is attributed to the formation of monomeric borane complexes from the borane dimer, eg, borane-tetrahydrofuran [14044-65-6] (1) or borane—dimethyl sulfide [13292-87-0] (2) (19—21). Stronger complexes formed by amines react with olefins at elevated temperatures (22—24). [Pg.308]

Retardation of the reaction rate by the addition of dimethyl sulfide is in accord with this mechanism. Borane—amine complexes and the dibromoborane—dimethyl sulfide complex react similarly (43). Dimeric diaLkylboranes initially dissociate (at rate to the monomers subsequentiy reacting with an olefin at rate (44). For highly reactive olefins > k - (recombination) and the reaction is first-order in the dimer. For slowly reacting olefins k - > and the reaction shows 0.5 order in the dimer. [Pg.309]

Borane—dimethyl sulfide complex (BMS) (2) is free of these inconveniences. The complex is a pure 1 1 adduct, ca 10 Af in BH, stable indefinitely at room temperature and soluble in ethers, dichioromethane, benzene, and other solvents (56,57). Its disadvantage is the unpleasant smell of dimethyl sulfide, which is volatile and water insoluble. Borane—1,4-thioxane complex (3), which is also a pure 1 1 adduct, ca 8 Af in BH, shows solubiUty characteristics similar to BMS (58). 1,4-Thioxane [15980-15-1] is slightly soluble in water and can be separated from the hydroboration products by extraction into water. [Pg.309]

Monohalogenoboranes are conveniendy prepared from borane—dimethyl sulfide and boron trihahdes (BX where X = Cl, Br, I) by redistribution reaction, eg, for monochloroborane—dimethyl sulfide [63348-81-2] (9) (81—83). Other methods are also known (84—87). [Pg.310]

The products are Hquids, soluble in various solvents and stable over prolonged periods. Monochloroborane is an equiUbtium mixture containing small amounts of borane and dichloroborane complexes with dimethyl sulfide (81). Monobromoborane—dimethyl sulfide complex shows high purity (82,83). Solutions of monochloroborane in tetrahydrofuran and diethyl ether can also be prepared. Strong complexation renders hydroboration with monochloroborane in tetrahydrofuran sluggish and inconvenient. Monochloroborane solutions in less complexing diethyl ether, an equiUbtium with small amounts of borane and dichloroborane, show excellent reactivity (88,89). Monochloroborane—diethyl etherate [36594-41-9] (10) may be represented as H2BCI O... [Pg.310]

Dihalogenoboranes are conveniently prepared by the redistribution of borane—dimethyl sulfide with boron trihaUde—dimethyl sulfide complexes (82,83), eg, for dibromoborane—dimethyl sulfide [55671-55-1] (14). [Pg.311]

Although dichloroborane reacts direcdy with alkenes in the gas phase (118), its complexes with diethyl ether and dimethyl sulfide are so strong that direct hydroboration does not proceed (119,120). The addition of a decomplexing agent, eg, boron trichloride, is necessary for hydroboration. [Pg.311]

Dibromoborane—dimethyl sulfide is a more convenient reagent. It reacts directly with alkenes and alkynes to give the corresponding alkyl- and alkenyldibromoboranes (120—123). Dibromoborane differentiates between alkenes and alkynes hydroborating internal alkynes preferentially to terminal double and triple bonds (123). Unlike other substituted boranes it is more reactive toward 1,1-disubstituted than monosubstituted alkenes (124). [Pg.311]

Among chiral dialkylboranes, diisopinocampheylborane (8) is the most important and best-studied asymmetric hydroborating agent. It is obtained in both enantiomeric forms from naturally occurring a-pinene. Several procedures for its synthesis have been developed (151—153). The most convenient one, providing product of essentially 100% ee, involves the hydroboration of a-pinene with borane—dimethyl sulfide in tetrahydrofuran (154). Other chiral dialkylboranes derived from terpenes, eg, 2- and 3-carene (155), limonene (156), and longifolene (157,158), can also be prepared by controlled hydroboration. A more tedious approach to chiral dialkylboranes is based on the resolution of racemates. /n j -2,5-Dimethylborolane, which shows excellent enantioselectivity in the hydroboration of all principal classes of prochiral alkenes except 1,1-disubstituted terminal double bonds, has been... [Pg.311]

Usually, organoboranes are sensitive to oxygen. Simple trialkylboranes are spontaneously flammable in contact with air. Nevertheless, under carefully controlled conditions the reaction of organoboranes with oxygen can be used for the preparation of alcohols or alkyl hydroperoxides (228,229). Aldehydes are produced by oxidation of primary alkylboranes with pyridinium chi orochrom ate (188). Chromic acid at pH < 3 transforms secondary alkyl and cycloalkylboranes into ketones pyridinium chi orochrom ate can also be used (230,231). A convenient procedure for the direct conversion of terminal alkenes into carboxyUc acids employs hydroboration with dibromoborane—dimethyl sulfide and oxidation of the intermediate alkyldibromoborane with chromium trioxide in 90% aqueous acetic acid (232,233). [Pg.315]

Through reaction with sulfide or elemental sulfur at 215°C, lignosulfonates can also be used in the commercial production of dimethyl sulfide and methyl mercaptan (77). Dimethyl sulfide produced in the reaction is further oxidized to dimethyl sulfoxide (DMSO), a useful industrial solvent (see Sulfoxides). [Pg.144]

Rectified oils have been redistilled to improve a particular property or characteristic, such as flavor or aroma. Eor example, natural oil of peppermint is frequently rectified to remove dimethyl sulfide, which has a powerful and objectionable cooked vegetable note deleterious to the use of the oil in cmme de menthe Hqueurs. Distillation is also used to remove psoralens, which are harmful photosensitizing agents present in natural bergamot oil. Color may be removed, eg, from cassia oil, by vacuum steam distillation. A desirable component, such as 1,8-cineole (eucalyptol) 85% in eucalyptus oil, may be... [Pg.296]

Reduction to Amino Alcohols. Reduction can be brought about using diborane—dimethyl sulfide in THF (80). NaBH in ethanol is also... [Pg.280]

Another product from kraft black Hquor is dimethyl sulfide. This chemical, which is added to natural gas to give it odor, is also oxidized to produce the versatile solvent, dimethyl sulfoxide (see Sulfoxides). [Pg.270]

Dimethyl sulfoxide occurs widely at levels of <3 ppm. It has been isolated from spearmint oil, com, barley, malt, alfalfa, beets, cabbage, cucumbers, oats, onion, Swiss chard, tomatoes, raspberries, beer, coffee, milk, and tea (5). It is a common constituent of natural waters, and it occurs in seawater in the 2one of light penetration where it may represent a product of algal metaboHsm (6). Its occurrence in rainwater may result from oxidation of atmospheric dimethyl sulfide, which occurs as part of the natural transfer of sulfur of biological origin (7,8). [Pg.107]

Thermal Stability. Dimethyl sulfoxide decomposes slowly at 189°C to a mixture of products that includes methanethiol, formaldehyde, water, bis(methylthio)methane, dimethyl disulfide, dimethyl sulfone, and dimethyl sulfide. The decomposition is accelerated by acids, glycols, or amides (30). This product mixture suggests a sequence in which DMSO initially undergoes a Pummerer reaction to give (methylthio)methano1, which is labile and reacts according to equations 1—3. Disproportionation (eq. 4) also occurs to a small extent ... [Pg.108]


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A-Chlorosuccinimide-dimethyl sulfide

Acrylic acid Dimethyl sulfide

Alkenes dibromoborane-dimethyl sulfide

Alkenes dichloroborane-dimethyl sulfide

Alkynes dibromoborane-dimethyl sulfide

Atmospheric flux, dimethyl sulfide

Atmospheric, dimethyl sulfide

Black liquor dimethyl sulfide

Borane complex with dimethyl sulfide

Borane complexes dimethyl sulfide

Borane s dimethyl sulfide as storable

Borane-Dimethyl sulfide-Sodium borohydride

Borane-dimethyl sulfide

Borane-dimethyl sulfide , hydride

Borane-dimethyl sulfide adduct

Borane-dimethyl sulfide dimer

Boron Compounds Borane-Dimethyl sulfide-Sodium

Boron trifluoride-Dimethyl sulfide

Chlorine reaction with dimethyl sulfide

Chloro borane-dimethyl sulfide

Copper bromide-Dimethyl sulfide

Copper bromide-dimethyl sulfide complex

Copper iodide-Dimethyl sulfide

Cuprous bromide-dimethyl sulfide complex

DIMETHYL SULFIDE.122(Vol

Dibromoborane-Dimethyl sulfide

Dichlorobis(dimethyl sulfide)platinum(II)

Dichloroborane-dimethyl sulfide

Dimethyl selenenyl sulfide

Dimethyl sulfide Dinitrogen

Dimethyl sulfide and N-chlorosuccinimide

Dimethyl sulfide and chlorine

Dimethyl sulfide boron complex

Dimethyl sulfide climate, global

Dimethyl sulfide cobalt complex

Dimethyl sulfide complex with dichloroborane

Dimethyl sulfide concentrations atmospheric

Dimethyl sulfide concentrations seawater

Dimethyl sulfide continental

Dimethyl sulfide ditriflate

Dimethyl sulfide emissions

Dimethyl sulfide halogen oxides, reactions with

Dimethyl sulfide hydroxyl radical reaction

Dimethyl sulfide hypochlorite

Dimethyl sulfide mixing ratios

Dimethyl sulfide natural emissions

Dimethyl sulfide niobium complex

Dimethyl sulfide nitrate radical reaction

Dimethyl sulfide over oceans

Dimethyl sulfide oxidation

Dimethyl sulfide ozonolysis workup

Dimethyl sulfide phytoplankton

Dimethyl sulfide platinum complexes

Dimethyl sulfide production

Dimethyl sulfide reaction

Dimethyl sulfide reaction sequence

Dimethyl sulfide reaction with base

Dimethyl sulfide reaction with phenol

Dimethyl sulfide reactions atmosphere

Dimethyl sulfide seawater

Dimethyl sulfide spectroscopy

Dimethyl sulfide structure

Dimethyl sulfide, DMS

Dimethyl sulfide, alkylation

Dimethyl sulfide, bond angle

Dimethyl sulfide, bond angle molecular model

Dimethyl sulfide, conversion

Dimethyl sulfide, conversion compounds

Dimethyl sulfide, derivative

Dimethyl sulfide, methionine methyl

Dimethyl sulfide, microbial metabolism

Dimethyl sulfide, molecular model

Dimethyl sulfide, protonation

Dimethyl sulfide, reaction with ozonides

Dimethyl sulfide, tropospheric

Dimethyl sulfide, tropospheric radical

Dimethyl sulfide, tropospheric sources

Dimethyl sulfide-Cuprous bromide

Dimethyl sulfide-Dibenzoyl peroxide

Dimethyl sulfide-Methanesulfonic acid

Dimethyl sulfide-chlorine

Formation from dimethyl sulfide

Formation of dimethyl sulfide

Halides, alkyl, reaction with dimethyl sulfide

Halogen oxides dimethyl sulfide reaction

Hydroborations dibromoborane-dimethyl sulfide

Hydroborations dichloroborane-dimethyl sulfide

Hydroperoxides with dimethyl sulfide

Hydroxyl radical dimethyl sulfide

Ketones dibromoborane-dimethyl sulfide

Monochloroborane-dimethyl sulfide

N-Chlorosuccinimide-Dimethyl sulfide

Phosphine sulfide, dimethyl

Phosphine sulfide, dimethyl manganese complex

Platinum(II) Complexes of Dimethyl Sulfide

Precursor of dimethyl sulfide

Reaction with dimethyl sulfide

Reduced Sulfur Compounds (Dimethyl Sulfide)

Reducing agents dimethyl sulfide

Reductive cleavage with dimethyl sulfide

Relationship with dimethyl sulfide

Scavengers dimethyl sulfide

Sulfide, dimethyl DMSO oxidation of alcohols

Sulfide, dimethyl acids

Sulfide, dimethyl alkenes, ozone

Sulfide, dimethyl carboxylic acid reduction

Sulfide, dimethyl chlorine activator

Sulfide, dimethyl diborane complex

Sulfide, dimethyl oxidative cleavage

Sulfide, dimethyl solvent

Sulfides dimethyl sulfide

Tetrabutylammonium Trichloro(dimethyl sulfide)platinum(II)

Thexylchloroborane-Dimethyl sulfide

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