Lithium diorganocopper compounds

These alkyllithiums can combine with Cul to form lithium diorganocopper compounds (R2CuLi), which are known as Gilman reagents. 

One particularly valuable reaction of alkyl lithiums is in making lithium diorganocopper compounds, LiR2Cu, by reaction with copper(I) iodide in... 

One of the most valuable reactions of alkyllithiums is their use in making lithium diorganocopper compounds, R2CuLi, called Gilman reagents. These reagents are easily prepared by reaction of an alkyllithium with cop-per(I) iodide, Cul, in ether solvent. 

How might conjugate addition reactions of lithium diorganocopper reagents be used to synthesize the following compounds ... 

Organomagnesium and Organolithium Compounds 15-2 Lithium Diorganocopper (Gilman) Reagents 15.3 Carbenes and Carbenoids... 

Formation of Gilman Reagents (Section 15.2A) Lithium diorganocopper (Gilman) reagents are prepared by treating an organolithium compound with copper(I) iodide. 

Show how to convert 1-bromopentane to each of these compounds using a lithium diorganocopper (Gilman) reagent. Write an equation, showing structural formulas, for each s)mthesis. 

Show how to prepare each compound from the given starting compound through the use of a lithium diorganocopper (Ghman) reagent. 

The lithium diorganocopper reaction has no direct counterpart in biological chemistry, although weTl see in Section 17.12 that conjugate addition of various other carbon-based nucleophiles to o , S-unsaturated carbonyl compounds does occur frequently in many biological pathways. 

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