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PPh3 with lithium naphthalcnide in THF at -108 "C. The resulting copper anion solutions are homogeneous and. like the zero-valent copper, readily undergo oxidative addition to carbon-halogen bonds. However, the copper anion is a two-equivalent electron reagent, and one equivalent of halide reacts with one equivalent of copper anion.

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.

The intermediate cyclized upon warming, affording the corresponding spirocarbocycle containing an exocyclic double bond. A wide variety of spirocycles were synthesized from the reactions of magnesium complexes of 1,2-dimethylenecyclopentane and 1,2-dimethylenecycloheptane with 1,n-dibromoalkanes as shown in Table 1-4. Therefore, this spiroannulation method provides a very general approach to a large number of spirocarbocycles with different combinations of ring sizes. 5 Synthesis of Fused Carbocycles, /3, punsaturated Ketones and 3-Cyclopentenols from Conjugated Diene-Magnesium Reagents With the aid of Rieke magnesium, fused carbocyclic enols can be effortlessly synthesized from 1,3-diene-magnesium complexes by reacting with carboxylic cstcrs [301.

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