| Autor: |
Shoji, Taku, Ito, Shunji, Okujima, Tetsuo, Higashi, Junya, Yokoyama, Ryuji, Toyota, Kozo, Yasunami, Masafumi, Morita, Noboru |
| Zdroj: |
European Journal of Organic Chemistry; April 2009, Vol. 2009 Issue: 10 p1554-1563, 10p |
| Abstrakt: |
Electrophilic ipsosubstitution reactions between 1,3,6tritertbutylazulene 2 and several electrophilic reagents were examined. Friedel–Crafts and Vilsmeier reactions of 2gave the corresponding ipsosubstitution products in moderate to excellent yields. One of the ipsosubstitution products, 1,6ditertbutyl3formylazulene 5, was converted in high yield into the synthetically more useful azulene derivative 1,6ditertbutylazulene 1 by decarbonylation on treatment with pyrrole in acetic acid. Treatment of 2with N[trifluoromethylsulfonyl]pyridinium trifluoromethanesulfonate TPT unexpectedly afforded 1trifluoromethylthioazulene 10and 18Hazulenone 11. Compound 2also reacted with tetracyanoethylene TCNE to give an excellent yield of cycloaddition product 13, rather than the ipsosubstitution reaction product.© WileyVCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009 |
| Databáze: |
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