Organolithium reagents with epoxides

Write equations for the reaction of organolithium reagents with water or epoxides. 

We saw an example of nucleophilic ring opening of epoxides in Section 15.4, where the reaction of Grignard and organolithium reagents with ethylene oxide was presented as a synthetic route to primary alcohols ... 

Organolithium reagents react with epoxides in a similar manner... 

A. Epoxide Ring Opening with Nonstabilized Organolithium Reagents... 

Few types of epoxide react with Grignard or organolithium reagents in the absence of catalysts without rearrangement. These include oxirane, which has been extensively used to transform these organometallic reagents into 2-substituted... 

Mechanism 14-4 Base-Catalyzed Opening of Epoxides 653 14-14 Orientation of Epoxide Ring Opening 654 14-15 Reactions of Epoxides with Grignard and Organolithium Reagents 656 14-16 Epoxy Resins The Advent of Modern Glues 656 Summary Reactions of Epoxides 658 EssentialTerms 660 Study Problems 662... 

The a-halo carbonyl compounds are reagents for the synthon +C-C=0. At a lower oxidation level, epoxides are reagents for the synthons +C-C=0 as in their reaction with Grignard or organolithium reagents (see also frames 162-6). 

The nucleophilic carbon of an organometallic compound reacts with an electrophile. For example, in the following reactions, the organolithium reagent and the Grignard reagent each react with an epoxide. 

Epoxides are opened with organolithium reagents, normally with attack at the less-substituted carbon atom of the epoxide. A potential competing reaction is proton abstraction adjacent to the epoxide, leading to an allylic alcohol. 

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