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The acidic condensation of bis (2-ethoxycarbonyl-5-indolyl) oxide and bis(2-ethoxycarbonyl-5-indolyl)methane with aromatic aldehydes was studied. Bis(3-chloro) compounds with labile chlorine atoms, by nucleophilic substitution of which the corresponding dimethylamino, hydroxy, methoxy, acetoxy, cyano, and mercapto derivatives were obtained, were isolated.

Some electrophilic substitution reactions in the di(5-indolyl) oxide series were studied. The Vilsmeier and Mannich reactions and diazo coupling and N-alkylation were realized. The di(5-indolyl) oxide molecule was subjected to quantum-chemical calculation.

Bis(2-carbethoxy-5-indolyl) oxide was obtained by cyclization of ethyl pyruvate 4,4′-diphenyloxydihydrazone. 5-Phenoxy-2-carbethoxyindole was also isolated from the reaction products. Saponification of these esters gave the corresponding acids, the thermal decarboxylation of which yielded di(S-indolyl) oxide and 5-phenoxyindole.