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By A. Furstner

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5 mL tetrahydrofuran (THF) in one flask. Once this mixture has stirred for about 20-40 sec, it will turn dark green, indicating the formation of lithium naphthalenide. 5 mL of THF is then cannulated dropwise (ca. 5 min after the transfer is complete. 531. A second method sometimes employed to prepare Rieke /inc uses a stoichiometric amount of naphthalene with respect to lithium. Both methods yield Rieke zinc with the same reactivity. It should also be noted that the reactivities are similar regardless of the choice of solvent (THF or DME) and that of the halide salt.

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.

Analogously, intramolecular cyclizations via an epoxide cleavage process can also be realized. For example, treatment of 6-bromo- 1,2-epoxyhexane with thienyl-based copper resulted in intramolecular cyclization; subsequent trapping of the intermediate with benzoyl chloride gave a 64 : 36 mixture of cyclohexyl benzoate and cyclopentylmethyl benzoate in 52% isolated yield as shown in Scheme 1-13. 52% (64:36) awi Scheme 1-13. Intramolecular cyclizations via epoxide cleavage. 5 Copper Cyanide-Based Active Copper Initial attempts to make active copper from CuCN .

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