Active Metals [chemistry] by A. Furstner

By A. Furstner

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The activation of the zinc surface could originate by the adsorption of the Lewis base cyanide ion on the metal surface. The adsorbed cyanide ion can affect the metal's reactivity in two possible ways. One possible mode of activation would be the reduction of the metal's work function in the vicinity of the adsorbed cyanide ion, and the second could be that the cyanide ion is acting as a conduction path for the transfer of the metal's electrons to the alkyl chloride. One or both processes could account for the observed enhanced chemical reactivity.

For example, 1,2-bis(rnethylene)cyclohexane-magnesium reagent was treated with cyclohexene oxide at -78 "C followed by the introduction of CO2 at 0 "C and acidic hydrolysis with subsequent warming to 40 "C. Work-up afforded the tricyclic spiro d-lactone, hexahydro-2'-methylene-spiro[4H-1-benzopyran-4,1 '-cyclohexanl2(3H)-one, in 63% isolated yield as a I :1 mixture of diastereomers (Table 1-8, entry 4). 18 I Ricke M e t d s : Highly Keuctirv Metcil Powders Tahle 1-7. Synthcsis of spiro-y-lactones from conjugated dimes, kctones and CO:.

Owed 1,4-conjugate additions to occur at -78 "C in good isolated yields, as shown in Table 1-28. 5 : 1. As with other spccies of active copper, compctitivc 1,2-addition products were not observcd The reactions of several non-functionalized allyl chlorides and acetates with active copper followed by cross-coupling with various electrophiles at - 100 "C gave ketone and alcohol products in good isolatcd yields. Although this species of active copper is not nucleophilic enough to undergo intramolecular or intermolecular epoxide-opening rcactions, the addition of MeLi enhances the nucleophilicity of the allylic organocopper rcagents and allows substitution reactions with epoxides.

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Active Metals [chemistry] by A. Furstner
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