Solvent Effect on the Reaction Site

Solvents are known to exert large effects on reaction rates, equilibrium constants, chemical reactions, and so on [35].

We have discovered that, in the reaction of 1-methoxy-3-(2-nitrovinyl)in-dole (123a) with nucleophiles (Scheme 16), the choice of the solvent also governs the reaction site [36]. The compound (123a) has two reaction sites. One is the ^-carbon of the nitrovinyl side chain at the 3-position giving the Michael addition product. The other is the 2-position with concomitant liberation of the 1-methoxy group producing 2-substituted indoles.

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