Sunday, April 3, 2011

Grignard Reaction

In organic chemistry, we were assigned to search for a reaction that involves the use of an organolithium, organocuprate, or Grignard reagent in at least one synthetic step. The one I found was called Di-n-Butyldivinyltin and it had a Grignard reaction involved. The reaction is shown below.
 


In the first part of the reaction, the vinyl bromide is added to magnesium and tetrahydrofuran (THF) is added and a Grignard reagent was produced called vinylmagnesium bromide. In the reaction, vinylmagnesium bromide used as a Grignard reagent to produce Di-n-Butyldivinyltin. Grignard reagents are formed more rapidly in tetrahydrofuran and are an important tool in the formation of carbon-carbon bonds. Grignard reagents are strong bases, and are not compatible with good leaving groups or proton acids. However, they add to epoxides and carbonyl groups, and can be used to make other organometallic reagents by reacting with metal-halogen bonds. A Grignard reaction first involves the preparation of an organomagnesium reagent with the reaction of an alkyl bromide with magnesium metal. Its nucleophilic character allows it to react with the electrophilic carbon in a carbonyl group and forms the carbon-carbon bond. Alkynylmagnesium halides and alkynyllithium reagents are useful nucleophiles for C-C bond synthesis.





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