With Organo Lithium Compounds

Reactions of tellurium tetrachloride with methyl lithium or pentafluorophenyl lithium yielded triorgano telluronium halides. 

Trimethyl Telluronium Iodide 250 ml of a 0.48 molar solution of methyl lithium (120 mmol) in diethyl ether are cooled under an inert atmosphere to — 70° and a solution of 7.8 g (29 mmol) of tellurium tetrachloride in too ml of diethyl ether is added dropwise with stirring. On completion of the addition, the mixture is allowed to warm to 20° and to stand at 20° for 30 min. It is then hydrolyzed with ice/water, and the aqueous phase is separated and added to a saturated aqueous solution of sodium iodide. Precipitated trimethyl telluronium iodide is collected and recrystallized from water yield 1.7 g (84%) sublimes between 213 and 257° 

The reaction of tellurium tetrachloride (9.3 mmol) with pentafluorophenyl lithium (24 mmol) in diethyl ether/hexane solution gave tris pentqfluorophenyl] telluronium chloride (m.p. 188-190°).  

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This procedure illustrates a general method for the preparation of alkenes from the pal 1 adium(Q)-cata1yzed reaction of vinyl halides with organo-lithium compounds, which can be prepared by various methods, including direct regioselective lithiation of hydrocarbons. The method is simple and has been used to prepare a variety of alkenes stereoselectively. Similar stoichiometric organocopper reactions sometimes proceed in a nonstereoselective... 

Sulfonium, cyclopropyldiphenyl tetrafluoroborate, 54, 28 Sulfonium salts, acetylenic, furans from, 53, 3 Sulfonium ylides, 54, 32 Sulfur, reaction with organo-lithium compounds, 50, 105 Sulfuryl chloride, with 1,1-cyclobutanedicarboxylic acid to give 3-chloro-l,1-cyclobutanedicarboxylic acid, 51, 73... 

Another method is to use a much less electrophilic acylating agent than an ester. This sounds crazy but DMF 20 reacts directly with organo-lithium compounds to give good yields of aldehydes... 

Snyder703 was the first to obtain an organo-lithium derivative of pyrazole, when he treated l-phenyl-3-methylpyrazole with butyl-lithium and then carbon dioxide, and isolated l-phenyl-3-methyl-pyrazole-5-carboxylic acid. Subsequently, Alley704 showed that 1-phenyl- and 1-methyl-pyrazoles are also metallated in the 5-position by the treatment with organo-lithium compounds. Hiittell and Schon705 studied the pyrazolyl lithium derivatives in detail, and showed that in pyrazole itself the 3- and 5-hydrogen atoms were more... 

Triorgano telluronium halides reacted with organo lithium compounds to produce tetraorgano telluriums5,6. 

Aminomethylotion. The reagent reacts with Grignard reagents to form N,N-bis(trimethylsilyl)amines in 60-90% yield (equation I). A similar reaction with organo-lithium compounds requires added magnesium biomide for satisfactory yields. ... 

A knowledge of the action of lithium alkoxides in these systems is important because they are always present to some extent, formed by fortuitous catalyst destruction by traces of oxygen. The other likely impurity is lithium hydroxide produced from traces of water in the system. It apparently decreases the initiation rate [53] but primarily [55] because it reacts with organo-lithium compounds... 

Reaction with organo-lithium compounds works well with all three examples one molecule of formaldehyde is lost but a CH2OH group is retained in the products 56, 57, and 58 from addition of vinyl, phenyl, and butyl lithium. This chemistry was used to make bertyodionol.7... 

Recently, William and co-workers [36] have produced a TiC coating with the product obtained from the reaction of the reactive titanium ethoxide with organo-lithium compounds as shown in eq. (12.18a). The product is isolated as yellow... 

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