Methyl lithium Methylmagnesium bromide

The 13C n.m.r. spectra of nicotine metabolites have been measured and discussed.39 The stereoselectivity of the iodomethylation of nicotine and seven analogues has been studied with the aid of 13C n.m.r. spectroscopy.40 Nicotine yields 2-methylnicotine as the major product when treated with methyl-lithium or methyl radicals, accompanied, as reported earlier, by 4- and 6-methylnicotine. Nicotine tV-oxide and methylmagnesium bromide afford 2- and 6-methyl-nicotines.41 Anabaseine (26), a well-known minor alkaloid of tobacco, has been identified as a poison-gland product in ants of the genus Aphaenogaster, which use it as an attractant.42... 

Reduction of (427) with lithium in liquid ammonia followed by trapping of the enolate with methyl iodide gave the pure 10/3-methyl compound, which was transformed into ( )-D-homotestosterone (428) by successive treatment with dilute aqueous acid at room temperature and with hot dilute aqueous methanolic sodium hydroxide. To synthesize ( )-progesterone, the carbonyl group of (428) was protected as its dioxolane, the alcohol oxidized, the derived 17a-ketone reacted with methylmagnesium bromide, the tertiary alcohol dehydrated, and the ketone deprotected to furnish the D-homo-17a-methyl-... 

Z)-alkene (3) is obtained with 887 stereoselectivity. Yields are lower if methyl-lithium is replaced by methylmagnesium bromide. Other alkyllithiums were also used. ... 

Methyl magnesium N-cyclohexylisopropylamlde, made from lithium cyclohexyllsopropylamide and methylmagnesium bromide, acts as a very efficient base catalyst to effect the isomerization shown in Scheme 7. ... 

The reduction of methyl 6-methoxy-2-naphthyl acetate with lithium aluminium hydride in refluxing ether gives 2-(6-methoxy-2-naphthyl)ethanol, which by treatment with PBr3 in refluxing benzene is converted into 2-(6-methoxy-2-naphthyl)ethyl bromide. Further reaction with KCN in refluxing ethanol-water affords 3-(6-methoxy-2-naphthyl) propionitrile, which is finally treated with methylmagnesium iodide in refluxing ethanol. 

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