Side-chain reactivity of indole derivatives. The reaction of 3-indolylmethyltrimethylammonium methyl sulphate with sodium toluene-p-thiolate

Abstract

The reaction of 3-indolylmethyltrimethylammonium methyl sulphate with sodium toluene-p-thiolate in methanol is of first order in both reactants; the bimolecularrate constants, k₂, decrease as the toluene-p-thiol concentration is increased. The plot of k₂ against [p-CH₃·C₆H₄·SH]^–1 is linear. The results fit an elimination–addition mechanism of the type suggested for nucleophilic substitutions of gramine. This is supported by kinetic results for the corresponding reaction of 3-(N-methyl)indolymethyltrimethylammonium iodide.