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Mechanistic studies with fluoromethyl IPP/DMAPP analogues. Compounds 16-18 are isomerized by IDI-2 at rates much slower than the native substrate (IPP) – paralleling the reactivity trends seen in the hydrolysis of 19, which is believed to proceed by an SN1 mechanism through a 3°cationic intermediate. This data is consistent with the formation of a carbocation intermediate or cation-like transition state in the IDI-2 catalyzed reaction.
