Transformations of Conjugated Enynones in the Superacid CF3SO3H. Synthesis of Butadienyl Triflates, Indanones, and Indenes

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• 作者：Steve Saulnier ; Alexander A. Golovanov ; Alexandr Yu. Ivanov ; Irina A. Boyarskaya ; Aleksander V. Vasilyev
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：March 4, 2016
• 年：2016
• 卷：81
• 期：5
• 页码：1967-1980
• 全文大小：650K
• ISSN：1520-6904

文摘

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.