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• W1973490509 abstract "Abstract Electrophilic ipso ‐substitution reactions between 1,3,6‐tri‐ tert ‐butylazulene ( 2 ) and several electrophilic reagents were examined. Friedel–Crafts and Vilsmeier reactions of 2 gave the corresponding ipso ‐substitution products in moderate to excellent yields. One of the ipso ‐substitution products, 1,6‐di‐ tert ‐butyl‐3‐formylazulene ( 5 ), was converted in high yield into the synthetically more useful azulene derivative 1,6‐di‐ tert ‐butylazulene ( 1 ) by decarbonylation on treatment with pyrrole in acetic acid. Treatment of 2 with N ‐[(trifluoromethyl)sulfonyl]pyridinium trifluoromethanesulfonate (TPT) unexpectedly afforded 1‐trifluoromethylthioazulene 10 and 1(8 H )‐azulenone 11 . Compound 2 also reacted with tetracyanoethylene (TCNE) to give an excellent yield of cycloaddition product 13 , rather than the ipso ‐substitution reaction product.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)" @default.
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• W1973490509 date "2009-03-13" @default.
• W1973490509 modified "2023-10-02" @default.
• W1973490509 title "Electrophilic <i>ipso</i>‐Substitution and Some Unique Reaction Behavior of 1,3,6‐Tri‐<i>tert</i>‐butylazulene" @default.
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• W1973490509 doi "https://doi.org/10.1002/ejoc.200801078" @default.
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