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Equimolar mixtures of n-butyllithium and potassium tert-amyloxide effect metallation and metal hydride elimination of cyclic olefins directly to give conjugated anions and polyanions in a single operation. 1-Methyl-1-cycloalkenes or methylenecycloalkanes are particularly well suited and give highly unsaturated products. Odd-membered rings eliminate better than their even-membered counterparts, and eight-membered rings eliminate particularly slowly. Reactions with methyl iodide and trimethylsilyl chloride proceed smoothly in high yield.
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Wilhelm et al. (1983) studied this question.
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