Abstract
The relationship between the structure of alkyl halides and the relative reactivity of nucleophilic centers existing in an ambifunctional nucleophilic system and in particular the alkylation reactions of the indole sodium salt in THF with primary, secondary, tertiary, allyl and benzyl halides has been investigated. In the course of alkylation of the indole salts, the reactivity of the less electronegative center (position 3 of the indole nucleus) increases the higher the SN 1 character of the reacting species and the greater the interaction of the cation with the ambient indole anion. This is in accordance with the results reported for pyrrole, enol and phenol ambident systems. For a number of alkyl, allyl and benzyl indole derivatives, the methods of separation and the spectrographic characteristics (IR, UV, NMR) of pure products are reported.
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