title: Transformations of Conjugated Enynones in the Superacid CF3SO3H. Synthesis of Butadienyl Triflates, Indanones, and Indenes.
abstract: Conjugated 1,5-diarylpent-2-en-4-yn-1-ones add the superacid CF3SO3H to the acetylenic bond with formation of the corresponding butadienyl triflates. Under superacidic reaction conditions, these triflates are transformed into indanone or indene derivatives depending on which substituents on the aromatic ring are conjugated with the butadiene fragment. In a less acidic system (10% vol pyridine in CF3SO3H) only the formation of butadienyl triflates takes place. Cationic reaction intermediates were studied by means of NMR and DFT calculations.
authors: Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University , Universitetskaya nab., 7/9, Saint Petersburg 199034, Russia.
authors: Steve
authors: S
authors: Saulnier
authors: Department of Chemistry, Chemical Processes and Technologies, Togliatti State University , Belorusskaya ul., 14, Togliatti, 445667 Russia.
authors: Alexander A
authors: AA
authors: Golovanov
authors: Center for Magnetic Resonance, Research Park, St. Petersburg State University , Universitetskiy pr. 26, Saint Petersburg, Petrodvoretz 198504, Russia.
authors: Alexandr Yu
authors: AY
authors: Ivanov
authors: Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University , Universitetskaya nab., 7/9, Saint Petersburg 199034, Russia.
authors: Irina A
authors: IA
authors: Boyarskaya
authors: Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University , Universitetskaya nab., 7/9, Saint Petersburg 199034, Russia.
authors: Aleksander V
authors: AV
authors: Vasilyev