Reactions of arylacetylenic compounds with arenes in the presence of aluminum halides

Conjugated arylacetylenic ketones and aldehydes, propargyl-type alcohols, and arylacetylenes reacted with arenes in the presence of AlBr₃ or AlCl₃ as catalyst to give substituted indenes. 3-Arylpropynoic acids under analogous conditions gave rise to 3,3-diarylindan-1-ones, while the corresponding methyl esters were converted into methyl 3,3-diarylprop-2-enoates. The key intermediates in the transformations of acetylenic ketones and aldehydes and propargyl-type alcohols into indene derivatives are resonance-stabilized propargyl—allenyl cations -C≡ C-C⁺ ? -C⁺=C=C which reacted with one of the resonance structures to give isomeric indenes, depending on the substituent nature.