A-Naphthyl magnesium bromide

In a 1-5-litre three-necked flask prepare a solution of a-naphthyl magnesium bromide from 12 2 g. of magnesium turnings as detailed under... 

This is prepared by the interaction of a-naphthyl magnesium bromide and bismuth bromide, the product being extracted from the decomposed Grignard residue by chloroform (yield, 60 per cent.). It forms pale... 

Diphenyl Naphthyl Telluronium Iodide1 10 g (28 mmol) of diphenyl tellurium dichloridc are dissolved in 250 ml of dry toluene. A solution of 1 -naphthyl magnesium bromide in diethyl ether is prepared from 17.4 g (84 mmol) of 1-bromonaphthalene. The solution of the tellurium compound is quickly poured into the freshly prepared Grignard solution, the mixture is shaken vigorously, and 20 ml of dilute hydrochloric acid are added immediately. The solution is decanted from the precipitate, the precipitate is dissolved in boiling water, silver chloride is added, and the mixture is heated. The mixture is then filtered, sodium sulfite is added to the filtrate, and the telluronium iodide is precipitated by the addition of potassium iodide yield 11.8 g (78%) m.p. 148° (from ethanol, ethanol/diethyl ether). 

From a-naphthyl mercuric bromide and ethyl magnesium bromide. ... 

The silanorbomenes 1, 2, and 3 can be synthesized according to the literature [1, 2]. Hydrogen chloride cleavage of 3 leads to the silicon chlorinated precursor of 13, which is obtained by a Grignard reaction with naphthyl magnesium bromide in high yield (86 %). Similarly, 15 is available from HCl cleavage of 1 and reaction of the latter with fluorenyl lithium. The silicon-chlorinated silacyclobutanes 7, 8, and 11 are synthesized by [2+2]-cycloaddition of dichloroneopentylsilene with isoprene and dimethylbutadiene, respectively [3],... 

R,5R)-2,2-DIMETHYL-a,a,a, a -TETRA(NAPHTH-2-YL)-1,3-DIOXOLANE-4,5-DIMETHANOL FROM DIMETHYL TARTRATE AND 2-NAPHTHYL-MAGNESIUM BROMIDE... 

The transformation was found to be stereospecific since [Dj]-trans-215a reacted with (2-naphthyl)magnesium bromide to give [Djj-216 with complete retention of the deuterium label. Under the same reaction conditions, the deuterium atom was completely eliminated from [Dj ]-ds-215b resulting in the unlabeled arylated alkene 216 and [Djj-naphthalene, which is consistent with a possible pathway outlined in Scheme 10.70. 

Benzyl a-naphthyl selenide, (C6H5.CH2)Se(C10H7).2—This selenide is produced when the complex obtained from magnesium a-naphthyl bromide and metallic selenium is treated with benzyl chloride. It forms small colourless prisms from alcohol, M.pt. 68° to 69° C. It yields a picrate, which separates from ether in orange-red needles, M.pt. 118° C. 

Di-a-naphthylarsenoxide, (CioH7)aAsO. — The interaction between magnesium a-naphthyl bromide and arseniotis oxide is represented as taking place as follows ... 

Di-a-naphthylarsenious sulphide, (CioH7)a-A sS, is formed either by the interaction of magnesium a-naphthyl bromide and arsenic trisulphide, or by treating the corresponding oxide or chloride with hydrogen sulphide in the usual way. The sulphide melts at 185° to 186° C. 

When freshly precipitated silver chloride is used instead of the bromide, a brown, granular powder is obtained. When dry it readily decomposes, evolving clouds of diphenyl fumes. The ratio of silver to phenyl appears to be as 1 1. With magnesium p-xylyl- and a-naphthyl bromides and the magnesium compound of p-bromodiphenyl ether, similar compounds are isolated,... 

Thallium di-a-naphthyl bromide, prepared from magnesium a-naphthyl bromide and thallie chloride, is a fawn, crystalline powder, melting at 272° C. and is completely soluble in cold pyridine, insoluble in toluene. 

Lead diphenyl di-a-naphthyl, Pb(C6ll5)2(CioH7)2. This is obtained as a snow-white, granular, crystalline powder by the interaction of lead diphenyl dibromide and magnesium a-naphth d bromide. The product melts at 197° C., lead separating at a higher temperature, and it is soluble in ether, benzene, or hot alcohol. It reacts with thallic chloride according to the equation ... 

Gomberg and Bachmann150151 obtained a large number of aromatic pinacols in good yield by reduction with the binary mixture magnesium-magnesium bromide or iodide. For example, /i-(2-naphthyl)-1,2-diphenyl-1,2-ethane-diol can be prepared as follows 151... 

Alternatively, the stereo-specific analysis can be carried out chemically. The TGs are partially hydrolyzed in the presence of ethyl magnesium bromide. The resulting diacylglycerols are isolated and their OH groups converted to urethane with (S)-l-(l-naphthyl)ethylisocyanate. The sn-1,3- and the diastereomeric sn-1,2-and 2,3-di-acylglycerol urethane derivatives are separated in a subsequent HPLC step. The fatty acid analysis of the urethanes show the distribution of the acyl residues in positions 1, 2 and 3. 

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