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2 LiBr. We also found it possible to make 2,3-disubstituted-l,3-butadiencsusing CuCN . LiRr and cross-coupling with 1,4-dichlor0-2-butyne. This reaction was very regiospecific, giving S N ~ products. ' Unfortunately, arylzinc compounds did not yield the S N ~product ' when reacted with 1,4-dichloro-2-butyne. However, when reacted with 1,4-ditosyloxy-2butyne, aryl and alkyl organozincs gave excellent yields of the Ss2' products. Table 1- 16 shows examples of this type of transformation. The use of Rieke zinc allows a wide varety of functional groups to be included [58].

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. The MeLi is believed to act as a "dummy" non-transfcrable ligand, presumably forming a higher-order cuprate. Primary and secondary allyl chlorides containing diverse functionalities are tolerated by the CuCN-based copper. -unsaturated ketone, epoxide, nitrile, alkyl acetate, ester, alkyl chloride, and carbamate functionalTable 1-27.

The Rieke zinc used in those reactions was prepared using anhydrous zinc bromide and potassium or sodium metal in refluxing tetrahydrofuran (THF) or I ,2-dimethoxyethane (DME) for 4 h. This was the same method as used for preparing active magnesium, which had been reported the previous year [521. 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.

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