Abstract
AbstractElectrophilic 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(8H)‐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)
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