Sodium iodide reaction with

The lactams 2-pyrrolidinone and lV-methyl-2-pyrrolidinone may be used to increase the solubility of carbohydrates in alcoholic reaction media. However, they cannot be used in the preparation of metal halide adducts, because of their tendency to associate, perhaps by complexing, with metal halide adducts.1 Amides are known to form complexes with metal halides. For example, sodium iodide combines with N, N-dimethylformamide to give Nal 3 N,N-dimethylformamide. Acetamide can form NaBr 2 acetamide and NaI-2 acetamide. 7... 

It reacts with sodium iodide and with lithium bromide in the same manner as trichloromethyl chloroformate, liberating iodine and bromine respectively. All the six chlorine atoms take part in this reaction, which is as follows ... 

Azulenes are halocienated by jy-bromosuccinimide or iV-chlorosuccinimide [42,47], or by copper(II) bromide or chloride [94], to give mixtures of 1- and 1,3-substituted azulenes. Pyridinium perbromide produces the dibromo derivative [95]. Mono- and di-iodo derivatives have been obtained by reaction with iodine monochloride [95], T -iodosuccinimide [42] or iodine in the presence of copper(II) acetate [94]. Iodine in the presence of sodium iodide reacts with azulene at room temperature to give a good yield of 1-iodoazulene the kinetics of this reaction are comparable to those of a reactive benzene derivative such as aniline [96]. 

The liberated protons may be titrated with a solution of sodium hydroxide in the presence of an acid-base indicator or with a pH-metric indication. Alternatively, one may use the iodate-iodide reaction with profit. A solution of the iodate-iodide... 

Thus, to name just a few examples, a nucleophilic aliphatic substitution such as the reaction of the bromide 3.5 with sodium iodide (Figure 3-21a) can lead to a range of stereochemical products, from a l l mbrture of 3.6 and 3.7 (racemization) to only 3.7 (inversion) depending on the groups a, b, and c that are bonded to the central carbon atom. The ring closure of the 1,3-butadiene, 3.8, to cyclobutene... 

Ethyl phenylethylmalonate. In a dry 500 ml. round-bottomed flask, fitted with a reflux condenser and guard tube, prepare a solution of sodium ethoxide from 7 0 g. of clean sodium and 150 ml. of super dry ethyl alcohol in the usual manner add 1 5 ml. of pure ethyl acetate (dried over anhydrous calcium sulphate) to the solution at 60° and maintain this temperature for 30 minutes. Meanwhile equip a 1 litre threenecked flask with a dropping funnel, a mercury-sealed mechanical stirrer and a double surface reflux condenser the apparatus must be perfectly dry and guard tubes should be inserted in the funnel and condenser respectively. Place a mixture of 74 g. of ethyl phenylmalonate and 60 g. of ethyl iodide in the flask. Heat the apparatus in a bath at 80° and add the sodium ethoxide solution, with stirring, at such a rate that a drop of the reaction mixture when mixed with a drop of phenolphthalein indieator is never more than faintly pink. The addition occupies 2-2 -5 hoius continue the stirring for a fiuther 1 hour at 80°. Allow the flask to cool, equip it for distillation under reduced pressure (water pump) and distil off the alcohol. Add 100 ml. of water to the residue in the flask and extract the ester with three 100 ml. portions of benzene. Dry the combined extracts with anhydrous magnesium sulphate, distil off the benzene at atmospheric pressure and the residue under diminished pressure. C ollect the ethyl phenylethylmalonate at 159-160°/8 mm. The yield is 72 g. 

It consists in treating a solution of sodium iodide in pure acetone with the organic compound. The reaction is probably of the S 2 type involving a bimolecular attack of the iodide ion upon the carbon atom carrying the chlorine or bromine the order of reactivities of halides is primary > secondary > tertiary and Br > Cl. 

In the flask were succesively placed 0.10 mol of the sulfinate (note 2), 25 ml of dry, pure HMPT (note 3), 4 g of powdered sodium iodide, 40 g of zinc dust and some boiling stones. After swirling for a few seconds the flask was connected with the other parts of the distillation apparatus, the system was evacuated immediately by means of the water pump (note 4) and the flask was then heated cautiously (free flame). A vigorous reaction started suddenly and the cumulene and part of the HMPT passed over. When the distillation had stopped completely... 

Iodide ion (I ) Alkyl chlorides and bromides are converted to alkyl iodides by treatment with sodium iodide in acetone Nal is soluble in acetone but NaCI and NaBr are insoluble and crystallize from the reaction mixture making the reac tion irreversible... 

Arrange the isomers of molecular formula C4H9CI in order of decreasing rate of reaction with sodium iodide in acetone... 

Wnte an equation clearly showing the stereochemistry of the starting material and the prod uct for the reaction of (S) 1 bromo 2 methylbutane with sodium iodide in acetone What is the configuration R or S) of the product" ... 

Methylene iodide [75-11-6], CH2I2, also known as diio dome thane, mol wt 267.87, 94.76% I, mp 6.0°C, and bp 181°C, is a very heavy colorless Hquid. It has a density of 3.325 g/mL at 20°C and a refractive index of 1.7538 at 4°C. It darkens in contact with air, moisture, and light. Its solubiHty in water is 1.42 g/100 g H2O at 20°C it is soluble in alcohol, chloroform, ben2ene, and ether. Methylene iodide is prepared by reaction of sodium arsenite and iodoform with sodium hydroxide reaction of iodine, sodium ethoxide, and hydroiodic acid on iodoform the oxidation of iodoacetic acid with potassium persulfate and by reaction of potassium iodide and methylene chloride (124,125). Diiodoform is used for determining the density and refractive index of minerals. It is also used as a starting material in the manufacture of x-ray contrast media and other synthetic pharmaceuticals (qv). 

Fig. 3. Synthesis of fluoxetine (31). 3-ChIoro-I-phenyl-I-propanol reacts with sodium iodide to afford the corresponding iodo derivative, followed by reaction with methylamine, to form 3-(methyl amin o)-1-phenyl-1-propan 0I. To the alkoxide of this product, generated using sodium hydride, 4-fluorobenzotrifluoride is added to yield after work-up the free base of the racemic fluoxetine (31), thence transformed to the hydrochloride (51)...

Ha.loisoquinolines, The Sandmeyer reaction is commonly used to prepare chloroisoquinolines from the amino compound. The corresponding hydroxy compounds are also used by treatment with chlorides of phosphoms. The addition of bromine to a slurry of isoquinoline hydrochloride in nitrobenzene gives a 70—80% yield of 4-bromoisoquinoline [1532-97-4J. Heating 1-chloroisoquinoline [19493-44-8] with sodium iodide andhydriodic acid gives 1-iodoisoquinoline [19658-77-6] (179). 

Trimethylsilyl iodide [16029-98-4] (TMSI) is an effective reagent for cleaving esters and ethers. The reaction of hexamethyldisilane [1450-14-2] with iodine gives quantitative conversion to TMSI. A simple mixture of trimethylchlorosilane and sodium iodide can be used in a similar way to cleave esters and ethers (8), giving silylated acids or alcohols that can be Hberated by reaction with water. 

Nucleophilic Reactions. Useful nucleophilic substitutions of halothiophenes are readily achieved in copper-mediated reactions. Of particular note is the ready conversion of 3-bromoderivatives to the corresponding 3-chloroderivatives with copper(I)chloride in hot /V, /V- dim ethyl form am i de (26). High yields of alkoxythiophenes are obtained from bromo- and iodothiophenes on reaction with sodium alkoxide in the appropriate alcohol, and catalyzed by copper(II) oxide, a trace of potassium iodide, and in more recent years a phase-transfer catalyst (27). 

Diaryhodostibines are usually obtained by the metathetical reaction of the chlorostibines with sodium iodide (111,112). Diphenylfluorostibine [6651-55-4] Ci2HioFSb, can be prepared from an organosiUcon species (113) ... 

Bromo-3-methyl-4-nitroisothiazole can be converted into the 5-iodo analogue by reaction with sodium iodide in acetone (65AHC(4)107). Halogen exchange also takes place when 4-bromo-3-methylisothiazole-5-diazonium chloride is treated with methyl methacrylate and hydrolyzed, giving the chloro compound (150) (72AHC(14)l). 

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