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The acid-catalyzed bridge cleavage reactions of 8-oxabi-cyclo [3.2.1.] octa-2,5-dienes (1) are of considerable synthetic as well as mechanistic interest since they potentially provide a direct route to aromatic tropylium systems (equation 1). We
now report the first example of this conversion and demonstrate its synthetic utility with the development of a new and convenient synthesis of 4,5-benztropones.
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