I'm trying to come up with a compound class in which iodine atom would be a bad leaving group both whether it leaves or takes charge with it (I know that $\ce{I^+}$ on its own would be horrible leaving group, but I'm thinking of a reaction where it oxidizes and so might leave forming a carbanion).

Aryl and vinyl carbons are both good candidates, but I'm wondering if some other compounds might work better or just as well.

So the question is about finding a compound $\ce{RR'(R'')C-I}$ such that both $\ce{RR'(R'')C^+}$ and $\ce{RR'(R'')C^-}$ are not stable. Or in other way, a compound with both $\mathrm pK_\mathrm a$ higher and $\mathrm pK_\mathrm b$ lower than that of aryl or vinyl.


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