Tetra-chloromethane

Dichloromethane trichloromethane and tetra chloromethane are widely known by their common names methylene chloride chloroform and carbon tetrachloride respectively... 

MeOH (0.122 mL, 3.0 mmol) was added dropwise to a stirred suspension of anhydride 57b (164 mg, 1.0 mmol) and quinidine (0.357 g, 1.1 mmol) in a mixture of toluene and tetra-chloromethane (1/1, 5 mL) at -55 °C under argon. The reaction mixture was stirred at this temperature for 60 h. During this period, the material gradually dissolved. Subsequently, the resulting clear solution was concentrated in vacuo to dryness, and the residue was dissolved in EtOAc. The solution was washed with 2N HCl and, after phase separation, followed by extraction of the aqueous phases with EtOAc the organic layer was dried (MgSO ), filtered and concentrated in vacuo to provide the corresponding hemiester (2//,35)-3-endo-methoxycarbonyl-bicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid as a white solid (192 mg, 98%, 99% ee by chiral-HPLC on the methyl 4-bromophenol diester). 

Murray, W.T., Kelly, J.W., and Evans, S.A., Jr., Synthesis of substituted 1,4-oxathianes, mechanistic details of diethoxytriphenylphosphorane — and triphenylphosphine/tetra-chloromethane — promoted cyclodehydrations and 13C NMR spectroscopy, J. Org. Chem., 52, 525, 1987. 

During the course of our work with DTPP, we became interested in developing other useful and effective cyclodehydrating "media" for diols and triols, with particular emphasis on TPP and tetra-chloromethane (CCI4). 

Alkanes can react with halogens (F2, CI2, Br2,12) to form alkyl halides. For example, methane reacts with chlorine (CI2) to form chloromethane (methyl chloride), dichloromethane (methylene chloride), trichloromethane (chloroform), and tetra-chloromethane (carbon tetrachloride). 

Acceptor numbers are less than 10 for nonpolar non-HBD solvents, they vary between about 10... 20 for dipolar non-HBD solvents, and they cover a wide range of about 25... 105 for protic solvents cf. Table 2-5). Surprisingly, benzene and tetra-chloromethane have stronger electrophilic properties than diethyl ether and tetrahy-drofuran. Acceptor numbers are also known for binary solvent mixtures [70, 213]. 

A further useful application of SC-CO2 as a reaction medium is the free-radical side-chain bromination of alkylaromatics, replacing conventional solvents such as tetra-chloromethane or chlorofluorohydrocarbons having no abstractable hydrogen atoms [920]. For example, bromination of ethylbenzene in SC-CO2 at 40 °C and 22.9 MPa yields 95 cmol/mol (1-bromoethyl)benzene, with practically the same regioselectivity as obtained in conventional tetrachloromethane as the solvent. Even the classical Wohl-Ziegler bromination of benzylic or allylic substrates using A-bromosuccinimide (NBS) can be conducted in SC-CO2 [920]. Irradiation of a solution of toluene, NBS, and AIBN (as initiator) in SC-CO2 at 40 °C and 17.0 MPa for 4 hours gave (bromomethyl)-... 

Separation of the mixture of C60/C70 proved to be a challenging task, particularly because of the poor solubility of the material in most organic solvents. While the solubility in benzene is about 5 mg/mL at 25 °C, the compound is soluble with difficulty at the same temperature in chloroform, dichloromethane, tetra-chloromethane, diethyl ether, tetrahydrofuran, H-hexane, n-pen-tane, and n-octane. The mixture of C )/C7o dissoives appreciabiy better in boiling cyclohexane, from which small black cubes crystallize out on cooling. The material did not melt below 360 C in a sealed tube the resulting sample redissolves in benzene, showing no sign of decomposition. 

Nonpolar solvents (such as hexane and tetra-chloromethane). 

The nonstoichiometric production of trichloromethane from tetra-chloromethane by Shewanella putrefaciens (Picardal et al. 1993). 

Synonyms and trade names methane tetrachloride, tetra chloromethane, Fasciolin, Freon 10, Necatorine, Tetrafinol, Tetraform, Tetrasol. 

Non-polar. A solvent in which the molecules do not possess a permanent dipole moment and consequently will solvate non-polar species in preference to polar species. For example, benzene and tetra-chloromethane are good solvents for iodine and paraffin wax, but do not dissolve sodium chloride. 

Data obtained from Liaw and Cbang Polymerization was carried out with bisphenol S (5.00 mmol) and TCP (7.50 mmol) in the organic solvent (37.5 mL) and water (30 mL) in the presence of catalyst (3.15 mmol) and sodium hydroxide (28.5 mmol) at room temperature for 2 h. Abbreviations DCM, dichloromethane TCM, tetra-chloromethane DCE, 1,2-dichloroethane MB, nitrobenzene. Measured at aconcentration of 0.5 gdL inDMF at... 

FIGURE 8.25 UV-Vis-NIR spectra of PPy-DBSA solutions in (a) chloroform, (b) chlorobenzene, and (c) tetra-chloromethane containing 0.02 g/dL of extra DBSA with the polymer concentration of 0.01 g/dL. (From Song, K.T., Synthesis of electrically conducting soluble poly pyrrole and its characterization. Ph.D. thesis, 2000. With permission.)... 

Diethyl 1-chloroalkylphosphonates 2 are key reagents for the preparation of different organic compounds. The diethyl 1-chloromethylphosphonate reacts readily with butylli-tium to give diethyl a-lithiochloromethylphosphonate, which on treatment with tetra-chloromethane gives the stable diethyl 1,1-dichloromethylphosphonate. The latter is suitable for the preparation of 1,1-dichloroalkenes [242 a,b]. 

Fig. 2. The intensity of the adsorption band at 1720 cirri in the IR spectra of their 10% solutions in tetra chloromethane.

Monohalogenated long-chain acids are most easily prepared from the appropriate hydroxy acid. Reaction with triphenylphosphine and tetra-chloromethane or tetrabromomethane occurs smoothly and with complete inversion. d-(-)-12-Hydroxystearic add is thereby converted to L-(+)-12-chlorostearic acid. Alternatively the alcohol can be converted to its methanesulphonate and then reacted with magnesium bromide in an-... 

PS CR polymerization degree 1-10000 US 0.4kD-2145kD Chloroform / tetra-chloromethane 4.5 / 95.5 vol. S/S.D/A Macroporous glass, pore radius 125°A, 25-32pm, 60x0.4cm... 

Polyoxyphenylene CR 30kD Chloroform / tetra-chloromethane 71/29 vol. Silica gel Lichrospher 300 30°C 0.5ml/min 10 il... 

Polycarbonate linear CR oligomers Chloroform / tetra-chloromethane 17/83 vol. Silasorb 600, D<100°A, 25x0.4cm, Iml/min lOpl UV... 

A versatile dehydration method has been presented by Appel in a review [1100]. The dehydration reagent is the two-component system triphenylphosphine/tetra-chloromethane, and a key role is played by (trichloromethyl)phosphonium chloride 1448. Due to its oxophilicity, 1448 forms the intermediate 1449, which stabilizes by forming the small, low-energy molecules triphenylphosphine oxide, chloroform, and the desired cyanide 1379. 

Typical procedure. 7-Chloro-3-cyano-2,3-dihydro- 7-methyl-l-oxo-S-phenyl- 7 H- 7,4-benzo-diazepine 1451 [1102] A mixture of triphenylphosphine (104.0 g, 0.4 mol), tetra-chloromethane (350 mL), dioxane (400 mL), and the carboxamide 1450 (65.5 g, 0.2 mol) was stirred at 80 °C for 90 min, in the course of which the amide dissolved and the solution became orange. The solvent was then evaporated in vacuo and the residue was redissolved in dichloromethane. The organic solution was washed with water and then concentrated in vacuo. The resulting oil crystallized on trituration with a little diethyl ether. The cmde product, which still contained some triphenylphosphine oxide, was recrystallized from ethanol to afford 47 g (76%) of pure product 1451 mp 208-210 °C IR v ax = 2266 cm (CN). 

In 1976, Farrall and Frechet described the bromination of 1% crosslinked polystyrene resins with bromine in the presence of catalytic amounts of thallium triacetate (TTA) or thallium(iii) chloride under reflux in tetra-chloromethane in the dark, which led to the bromo-polystyrene products with highly reproducible degree of functionalisation, typically from 0.39 to 0.45. According to the authors, the degree of functionalisation was independent of the catalyst loading and was a function of the amount of bromine used. The polymers thus obtained were colourless as well as cleaner compared to those obtained by bromination catalysed by classical iron(iii) chloride. 

Figure 3.7 Correlation between infrared shifts Av (cm ) and proton resonance shifts Av (ppm) for solutions of salts in methanol. The origin is the point for monomeric methanol in tetra-chloromethane. The key, together with the solvation number required to fit the correlation, is...

Mej S -O, which is pyramidal and hence has an exposed dipole, produces the largest shift whereas non-dipolar solvents such as hexane or tetra-chloromethane (CCI4) are treated as causing zero shifts for condensed systems such as these. Often, the shifts are to lower frequencies when hydrogen bonds form, as in this case. The shift from zero is proportional to the total H-bond strength, but the individual shifts decrease as the number of bound water molecules increases. This is another example of the anti- cooperativity principle. 

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