Magnesium phenyl- iodide

The dichloride reacts with magnesium phenyl bromide, CeHs.MgBr, in ether solution, with formation of diphenyl telluride, (C6H5)2Te. Tellurium dibromide and di-iodide give a similar result.8 In ether solution the dichloride absorbs bromine and iodine, but the products, presumably the chlorobromide and chloro-iodide, respectively, have not been isolated.9... 

Acetophenone and magnesium methyl iodide yield 2-phenyl-l-propene. As can be seen from the equation, one at least of the radicals R, R1 Ru, must have a non-tertiary carbon linked in the intermediate compound to the hydroxy-magnesium-iodide carbon. 

Benzaldehyde and magnesium phenyl bromide or iodide give diphenyl carbinol. 

Cuprous phenyl, CuPhU—Cuprous iodide is added to a cold solution of magnesium phenyl bromide in ether. Complete solution takes place, and after a time the cuprous phenyl separates out as a white powder. It decomposes at 80° C. and when warmed with benzene is converted quantitatively into diphenyl and metallic copper, the latter appearing as a mirror. With water, benzene and cuprous oxide are formed, and with dilute nitric acid it is changed to nitrobenzene, concentrated nitric acid causing the compound to explode. Cuprous phenyl blackens in a few days, even when kept in a vacuum. 

The interaction of trimethyl boric ester and magnesium metliyi iodide in ether, followed by decomjiosition with acidified water, yields methyl boric acid, as white crystals, very volatile and unstable. It has never been isolated in the pure state, but Michaelis and Becker showed that it exerts a methylating action on magnesium phenyl bromide, the products consisting of phenyl boric acid and toluene. The esters of this acid are readily hydrolysed by cold water. 

Methylphenyl-p-tolylphosphine, (CH3)(CgH5)(C7H7)P, occurs when phenyl-p-tolylchlorophosphine reacts with magnesium methyl iodide, the best proportions being four molecular proportions of Grignard reagent to one of secondary phosphine. ... 

Organometallic reagents and alkali metal amides can react via a cyclic transition state (Section II, B, 5) beginning with electrophilic attack at the most basic ring-nitrogen. As a result, sodamide (in dimethylaniline, 145°, 2 hr) yields the 4-amino derivatives (40% yield S)) methyl- or phenyl-magnesium iodides give the 4-adduct quantitatively.s ... 

C. (E)- -Iodo-4 -phenyl-2-butene. In a 20-ml., round-bottomed flask are placed 2.0 g. (0.008 mole) of 2-(4/-phenyl-l -buten-3 -yl)thio-2-thiazoline, 5 ml. of methyl iodide [Methane, iodo-], and 2 ml. of di-methylformamidc. The resulting solution is heated at 75-80° for 2.5 hours under a nitrogen atmosphere (Note 13), cooled, and poured into 10 ml. of water. Extraction with three 12-ml. portions of ether separates the product from water-soluble by-products. The extracts are combined, washed with 8 ml. of 1% aqueous sodium thiosulfate and two 8-ml. portions of water, dried over anhydrous magnesium sulfate, and filtered to remove the drying agent. Removal of ether by distillation at 30° (100 mm.) leaves 1.5-1.7g. (74-82%) of ( )-l-iodo-4-phenyl-2-butene (Notes 14 and 15). 

Fujisawa et al. [Ill] have reported that the magnesiiun complex prepared from chiral 2-[2-[(tolylsulfonyl)amino]phenyl]-4-phenyl-l,3-oxazoline 81 and methyl-magnesium iodide was efficient, in a stoechiometric amount, for promoting the enantioselective Diels-Alder reaction of 3-alkenoyl-l,3-oxazohdin-2-one with cyclopentadiene (Scheme 45) leading exclusively to the endo adducts in up to 92% ee. The use of 10 mol% of the complex led to an important decrease in enantioselectivity of the product (51% ee). 

Phenyl thienyl ketone has been prepared by treatment of benzoyl chloride with thienylmercuric chloride 1 by treatment of thiophene with benzoyl chloride in the presence of thienylmercuric chloride,2 phosphorus pentoxide,3 stannic chloride,4 and aluminum chloride.5 It has also been prepared from thienyl-magnesium iodide and benzonitiile.6... 

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