Abstract
Abstract The palladium-catalyzed hydrogenolysis of 7-chloro-7-fluoro-1-phenyl-, 7-fluoro-1-phenyl-, and 7,7-difluoro-1-phenylbicyclo[4.1.0]heptane was investigated. The hydrogenolysis of the cyclopropane ring occurs at the C1–C6 bond selectively, accompanied by the elimination of the endo-halogen. The hydrogenolysis of endo-7-fluoro-1-phenylbicyclo[4.1.0]heptane proceeded rapidly to give phenylcycloheptane as a sole product, whereas exo-7-fluoro-1-phenylbicyclo[4.1.0]heptane reacted slowly to give trans-1-fluoro-2-phenylcycloheptane, accompanied by a small amount of the C1–C7 bond-cleaved product. The different reactivity between the endo and exo derivatives became more considerably by the introduction of a methyl group at the 2-position. Thus, with the compounds having 2-methyl group the endo-fluoro derivative was cleaved at the C1–C6 bond accompanied by the C1–C7 bond cleavage, whereas the exo-fluoro derivative was cleaved at the C1–C7 bond exclusively.
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