Abstract: | Methyl substituted bisindolylcarbenium ions 1 react with some O- and C-nucleophiles regioselectively. The cations 1b, 1c yield with hydroxide ions the tetraindolyldimethyl ether 4 and with methoxide ions the bisin-dolylmethoxymethanes 5. Compounds 1a, 1b, 1c react with several methylindoles to isomeric bis- and trisin-dolylmethanes. An electrophilic reactivity order of cations 1 can be derived supporting on the experimental results. |