Side-chain reactivity of indole derivatives. The reaction of 3-indolylmethyltrimethylammonium methyl sulphate with sodium toluene-p-thiolate
- 1 January 1968
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society B: Physical Organic
- p. 401-403
- https://doi.org/10.1039/j29680000401
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.Keywords
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