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| Abstract |
Treatment of 4-bromo-(1a), 4-chloro-2, 4, 6-tri-tert-butyl-(1b), 2, 4-dibromo-4, 6-di-tertbutyl-(1c), and 2-chloro-4-bromo-4, 6-di-tert-butyl-2, 5-cyclohexadien-1-one(1d) with silver perchlorate in be...nzene afforded various phenols produced via rearrangement of atom falogen, dehalogenation and/or de-tert-butylation. When 1b was treated with trifluoroacetic acid or silica gel in benzene, 2-chloro-4, 6-di-tert-butylphenol was obtained in good yield. Similarly, treatment of 1a with trifluoroacetic acid afforded 2-bromo-4, 6-di-tert-butylphenol. However, when 1a was column chromatographed on silica gel using benezene as an eluent, 2, 4, 6-tri-tert-buthlphenol was formed in good yield.show more
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