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Myers Magnesium-Halogen Exchange Chem 215
Review : • Unlike many lithium-halogen exchange protocols, only one equivalent of i-PrMgX is used
in typical experimental procedures.
Knochel, P.; Dohle, W.; Gommermann, N.; Kneisel, F. F.; Kopp, F.; Korn, T.; Sapountzis, I.;
Ahn Vu, V. Angew. Chem., Int. Ed. Engl. 2003, 42, 4302.
• THF is the most common solvent. Ethyl ether has been employed as a solvent for
selective exchange of geminal dihalides to generate magnesium carbenoids.
General References on the Preparation and Reactions of Grignard Reagents:
Main Group Metals in Organic Sy nthesis, Yamamoto, H., Oshima, K., Eds.; John Wiley and • The reactivity of Grignard reagents is highly temperature dependant. Only highly reactive
Sons: New York, 2004. electrophiles such as aldehydes and ketones react at significant rates below 0 °C. This
allows for the preparation of organomagnesium reagents containing cyano, nitro, ester,
Handbook of Grignard Reagents, Silverman, G. S., Rakita, P. E., Eds.; Marcel Dekker: and imine functional groups, provided that the rate of the exchange reaction is fast enough
New York, 1996.
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