Lithium salt of

Thus o-hydroxyphenyl-llthium cannot be obtained from o-bromophenol and lithium but, under proper conditions, o-bromophenol reacts with n-butyl-lithium to give a good yield of the lithium salt of o-hydroxyphenyl-hthium. An interesting application is to the preparation from m-bromochlorobenzene and M-butyl-lithlum of w-chlorobenzoic acid—an expensive chemical ... 

Some di-p-tolyl ketone is produced as a by-product, presumably by Interaction of the lithium salt of the carboxylic acid with the aryl lithium ... 

Ionic polymers may exist as undissociated, unsolvated ion pairs undissociated ion pairs solvated to some extent solvated ions dissociated to some extent or some combination of these. The propagation rate constant kp and the dissociation equilibrium constant K of the lithium salt of anionic... 

CH2(CF2CH2 2,4, been synthesized by the reaction of PCl and the lithium salt of the respective polyfluoroalkyl alcohols followed by... 

The metallic salts of trifluoromethanesulfonic acid can be prepared by reaction of the acid with the corresponding hydroxide or carbonate or by reaction of sulfonyl fluoride with the corresponding hydroxide. The salts are hydroscopic but can be dehydrated at 100°C under vacuum. The sodium salt has a melting point of 248°C and decomposes at 425°C. The lithium salt of trifluoromethanesulfonic acid [33454-82-9] CF SO Li, commonly called lithium triflate, is used as a battery electrolyte in primary lithium batteries because solutions of it exhibit high electrical conductivity, and because of the compound s low toxicity and excellent chemical stabiUty. It melts at 423°C and decomposes at 430°C. It is quite soluble in polar organic solvents and water. Table 2 shows the electrical conductivities of lithium triflate in comparison with other lithium electrolytes which are much more toxic (24). 

Reaction with Carbon Nucleophiles. Unactivated a2iddines react with the lithium salts of malonates or p-keto esters in the presence of lithium salts to yield 3-substituted pyttohdinones (56—59), where R = alkyl and aryl, and R = alkoxyl, alkyl, and aryl. 

Products from aminoalcohols and TYZOR TPT were obtained by a2eotropiag the isopropyl alcohol with ben2ene (121,122). From trimethylethylenediamine, dimethylethanolamine, and dimethylisopropanolamine with TYZOR TPT, the orange (11), the yellow (12), and the pale-green (13) were obtained, respectively. The lithium salt of the ligand, derived from C H Li, combiaed with (RO)2TiCl ia hexane has also been used (123). 

The synthesis of 3-acyl- and 3-aroyl-l,2-benzisoxazoles was accomplished by the desulfurization of (562). The dithioacetal (562) was prepared by the addition of the lithium salt of propenedithioacetal to an isocyanate with subsequent base cyclization (equation 61) (B-79MI41609). 

Lithium metal in ammonia at high concentration (4 M), with an alcoholic proton donor, will reduce the benzene ring of a phenoxide ion. The lithium salt of estrone is reduced under such conditions in 95% yield to a mixture containing 77% of estr-5(10)-ene-3a,17i -diol and 23% of the derived 5(10)-dihydro derivative. 

Polyfunctional fluoronitro alcohois are provided by tlie SRNl reaction of a perfluoroalkyl iodide or alkylene diiodides with the anhydrous lithium salt of 2-nitropropane l,3-diol acetonide. Hydrolysis of the resulting perfluoroalkyl-... 

Perfluorobenzene undergoes Sf Ar reactions readily with dimethylarmne, aniline, N methylaniline [AS], piperidine, A/-tnmethylsilyliminotnmcthylphos-phorane [69], and bthinm aniUde [70], but the reactions are often accompanied by sigmficant amounts of di- or polysubstitubon However, with the lithium salt of A -tnmethylsilylanilme, only one fluorine atom in pcrfluorobenzeneis replaced [71] (equation 36)... 

Various combinations of Rf and R (equation 36) have been studied [39, 72, 73, 74, 75], and it appears that the stability of the lithium salt of the hemiketal is the major factor in determming the reaction products formed via paths A, B, or C in equation 37 Other important factors that affect the course of the reacbon are (1) thermal stability of the perfluoroalkyllithium compounds, (2) reaction temperature, (3) mode of addition of the reactants, (4) stenc hindrance, (5) nature of the Y group (in equation 36), and (6) temperature at which the reaction is terminated by acid hydrolysis... 

Thiophenedithiol (170) has been prepared by halogen-metal interconversion between the lithium salt of 4-bromo-3-thiophenethiol and n-butyllithium at —70°C, followed by reaction with sulfur/ IR, NMR, and UV spectra showed that this compound exists in the dithiol form (170). The compound obtained as a by-product in the... 

Heating 3,4-bis(phenylsulfonyl)furoxan with a solution of sodium butoxide in butanol followed by reduction with trimethyl phosphite gives furazan 281 (Scheme 183). Compound 281 was converted into dialkoxy derivative 282 with the lithium salt of ( )-l-azabicyclo[2.2.2]octan-3-ol in 33% overall yield (96W012711, 97EUP773021, 98JMC379). 

Because of the lower stability of Se(IV) compounds as compared with their Te(IV) analogues (95UK527), the reaction of the disilyldiimine with SeCU ends up in phenanthro[9,10-c]-l,2,5-selenadiazole. 3,4-(2,4-Di-terr-butylbenzo)-l,2,5-telluradiazole 75 was obtained by a treatment of the tellurium diimide 76 with a lithium salt of tris(rerr-butyl)aniline. Dimer 77 is an intermediate in this reaction (96IC9). 

The same type of reaction occurs in the work of Hauptman (76T1293), who, studying the chemistry of diethynylcarbenes, found that the pyrolysis of the lithium salts of diethynylketone tosylhydrazones 5 (140-150°C) in the presence of olefins leads to cyclopropanes. This process results in the formation of the corresponding 3-ethynylpyrazoles. The formation of l-p-tolylsulfonyl-3-alkynylpyrazoles from hydrazone runs in milder conditions (50°C, 14 h) (Scheme 24). 

The lithium salt of 2-(di-wo-propylamino)-l,2-thiaborolide with [( -Cp ) RuC1]4 or [(i -Cp )ZrCl3] yields sandwiches similar to 39 (M = Ru, ZrCl2) (OOOM4935). The same anionic ligand enters a sequence of reactions with dimethylchlorosilane, lithium cyclopentadienyl, lithium di-wo-propylamide, and zirconium(IV) chloride to give sandwich 41. 

Interaction of iron(II) chloride with the lithium salt of R4B2NJ (R = Me, Et) gives sandwiches 61 (R = Me, Et) (67ZAAC1, 96MI4), resembling in electronic properties those of ferrocene (99ICA(288)17). The n- rf-) complex stems from the further complex-formation of 61 (R = Me, Et) with mercury(II) salts via the unsubstituted nitrogen atom. 

Reaction of 2-chloromethyl-4//-pyrido[l,2-u]pyrimidine-4-one 162 with various nitronate anions (4 equiv) under phase-transfer conditions with BU4NOH in H2O and CH2CI2 under photo-stimulation gave 2-ethylenic derivatives 164 (01H(55)535). These alkenes 164 were formed by single electron transfer C-alkylation and base-promoted HNO2 elimination from 163. When the ethylenic derivative 164 (R = R ) was unsymmetrical, only the E isomer was isolated. Compound 162 was treated with S-nucleophiles (sodium salt of benzyl mercaptan and benzenesulfinic acid) and the lithium salt of 4-hydroxycoumarin to give compounds 165-167, respectively. 

One of the syntheses of f1 udalanine begins with base promoted condensation of ethyl fluoroacetate and ethyl oxalate to give This is then converted by hydrolytic processes to the insoluble hydrated lithium salt of fluoropyruvate (58). This last is reductively aminated by reduction with sodium boro-deuteride and the resulting racemate is resolved to give D-flu-dalanine (59). 

The key intermediate 25 was prepared efficiently from aldehyde 23, obtained by reduction of nitrile 22 with Dibal-H. Treatment of 23 with the lithium salt of frans-diethyl cinnamylphosphonate furnishes compound 24 in 75 % yield and with a 20 1 ratio of E Z olefin stereoisomers. The stage is now set for the final and crucial operations to complete the molecular skeletons of endiandric acids A and B. 

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