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I know that cyclopropyl methyl carbocation is exceptionally stable and in fact more stable than benzyl carbocation but I was wondering if it was the same case with cyclopropyl methyl carbanion. Is it also more stable than benzyl carbanion?

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Sigma resonance only works on cyclopropyl methyl carbocation (and its cyclopropyl derivatives). So I don't think that cyclopropyl methyl carbanion will be exceptionally stable.

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  • $\begingroup$ Could you explain why sigma resonance only applies for cyclopropyl methyl carbocation. $\endgroup$ – Abhishek Mhatre Feb 4 '17 at 6:40

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