Alkylmagnesium dialkylamides

NR R" Alkylmagnesium dialkylamide Alkyl(dialkylamino)magnesium or alkyl(jV,. /V- dialkylaminato)magnesium... 

Although other methods are available for synthesizing alkylmagnesium dialkylamides, alkoxides and thiolates, the reaction of a dialkylmagnesium compound with a secondary amine, an alcohol, or a thiol, provides a convenient general method. Some examples are summarized in Table 3.11. 

To a suspension of the alkylmagnesium bromide (50 mmol, 25 % excess) in THF (200 mL, cooled to — 78 °C) was added Ti(0-i-Pr)4 (20 mmol) in THF (10 mL) under Nj through a steel cannula. After the mixture had been stirred for 2 min, the dialkylamide (20 mmol) in THF (10 mL) was added, and the mixture allowed to warm to 20 °C. After stirring for an additional 3 h volatile amines (with boiling points elose to that of THF and i-PrOH) together with THF were distilled from the reaction mixture, without adding water, under reduced pressure (lOOTorr) into a cold trap (— 78" C). Addition of a solution of HCl in EtjO precipitated the hydrochloride of the cyclopropylamine. The crystals were collected and recrystallized (CHCh/EtjO). 

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