Two convenient methods for the preparation of p-dialkylaminophenylacetylenes are reported: a) Dehydrobromination of the brominated compounds obtained easily from the dialkylamino substituted cinnamic acids in acetic acid instead of chloroform; b) dehydrochlorination of the 2-chlorostyrene derivative obtained from the reaction of p-dimethylaminobenzaldehyde with chloromethylenetriphenylphosphorane.
The acetylenic analogs of malachite green, crystal violet, and their related compounds have been synthesized to examine an effect of an acetylenic bond on a dye system.
1-Arylethyltriphenylphosphonium bromides thermally rearranged to 2-arylethyltriphenylphosphonium bromides. Direct formation of 2-arylethylphosphonium bromides was achieved by reacting styrene, HBr, and triphenylphosphine. On the other hand, thermolysis of 1-indanyltriphenylphosphonium bromide gave indene and triphenylphosphonium bromide. From deuterium and 13C-labeled experiments, the interconversion of primary and secondary cation intermediates was suggested. No neighboring phenyl group (phenonium cation intermediate) interaction was observed.
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