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New polyhalogenated benzobarrelenes were synthesized in good yields. The bromination reaction of benzobarrelenes at high temperature gives non-rearranged products. Dehydrobromination of the formed products with t-BuOK yielded the desired polyhalogenated benzobarrelenes. The elimination reaction of cyclopropanoid dibromide with a base unusually resulted in the formation of a benzosemibullvalene derivative.
Homobenzonorbornadiene and benzobarrelene were reacted with dimedone/acetylacetone and Mn(OAc) 3 in the presence of Cu(OAc) 2 in acetic acid. Mainly rearranged products having a [2.2.2]skeleton and the nonrearranged dihydrofuran derivatives were obtained. These observations clearly indicated that the second oxidation takes place before the cyclization reaction. Furthermore, intramolecular...
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