Convenient and General Synthesis of 2-Alkoxy-3-arylcyclopropenones

Cyclopropenylium Cations, Cyclopropenones, and HeteroanaloguesRecent Advances

“…The possible product, trialkoxy(aryl)cyclopropene or dialkoxy(aryl)cyclopropenylium ion, is readily hydrolyzed to give the ketones. 215 Reaction of trichlorocyclopropenylium ion with 1-trimethylsilyl-1-propyne 14 and trichloroethene 216 gave dialkynyl-and dialkenylcyclopropenones, respectively (eq 141).…”

Elimination Strategy for Aromatic Acetylenes

“…Decarbonylation of cyclopropenones, which has been briefly discussed in section 2.6, was utilized for the synthesis of aromatic acetylenes. Thus, photolysis of 2-alkoxy-3-arylcyclopentenones, prepared from cyclopropenium ions, provided acetylenic ethers (Scheme ) . West made use of this method for obtaining an acetylene with anthrylphenol moieties 82 (Scheme ). , Oxidation of 82 with PbO 2 afforded quinone 83 .…”

Recent Advances in Cyclopropene Chemistry

“…Monoarylation of 37, using one equivalent of an arene followed by alcoholysis, produced dialkoxycyclopropenylium species 43 (Scheme 31). 69 The latter, after hydrolysis, afforded 2-alkoxy-3-arylcyclopropenones 44, useful pre-cursors for alkoxyarylacetylenes via thermal or photochemical CO extrusion. 69…”

“…69 The latter, after hydrolysis, afforded 2-alkoxy-3-arylcyclopropenones 44, useful pre-cursors for alkoxyarylacetylenes via thermal or photochemical CO extrusion. 69…”