Abstract
Abstract 5,8-Dihydro-5,8-methanophthalazine, prepared by the reaction of bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarbaldehyde with hydrazine, reacted with MCPBA to give an N-oxide. Further oxidation with MCPBA afforded the corresponding exo-6,7-epoxy derivative. Treatments of the epoxide and its diphenyl-substituted derivative with trifluoroacetic acid gave 6,9-bis(trifluoroacetoxy) derivatives by a regioselective ring-opening of the oxirane, accompanied by Wagner–Meerwein rearrangement. The bis(trifluoroacetoxy) derivatives were converted to the corresponding diols for elucidation of their regio- and stereochemistry.
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