Magnesium, phenyllithium derivative

Metalation. Benzene reacts with alkali metal derivatives such as methyl or ethyUithium in hydrocarbon solvents to produce phenyllithium [591-51-5], C6H5Li, and methane or ethane. Chloro-, bromo-, or iodobenzene will react with magnesium metal in ethereal solvents to produce phenylmagnesium chloride [100-59-4], C6H5MgCl, bromide, or iodide (Grignard reagents) (32). 

There is very little known about the structure of the Lycopodium alkaloids. Where the determinations have been made, the nitrogen atoms have always proved to be tertiary without A -methyl, and methoxyl groups are absent. The oxygen in lycopodine is ketonic (19) as indicated by its infrared spectrum, the formation of a hydrazone, reduction to a carbinol, and reaction with phenyllithium to yield a tertiary alcohol although phenyl magnesium bromide does not react with it (20). Dihydrolycopodine (9) yields an 0-acetyl derivative melting at 96° and this and its perchlorate proved to be identical with alkaloid L2 and its perchlorate, respectively. When heated with selenium at about 310°, lycopodine generates 7-methyl-... 

Syntheses of RM(CO)5 compounds by reaction of [M(CO)5] with halides or by decarbonylation of acyl derivatives have been described. A third synthesis involves treatment of the pentacarbonyl halides M(CO)5X with an organic derivative of lithium or magnesium. Examples of this reaction include the treatment of Mn(CO)5Br with benzylmagnesium chloride to give the benzyl derivative C6H5CH2Mn(CO)5 93) and the reaction of Mn(CO)sBr with phenyllithium to give the phenyl derivative CsHsMn (CO)5 156). Disadvantages of reactions of this type include the formation of much Mn2(CO)io as a by-product and a low yield of the desired product. 

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