An oxidative rearrangement of 6-phenylbicyclo[3.2.0]heptan-6-ol to 1,1'-biphenyl-carbaldehydes: A mechanistic study

[摘要]：Acid-catalyzed rearrangement of 6-phenylbicyclo[3.2.0]heptan-6-ol gave 1,1'-biphenyl and 1,1'-biphenyl-carbaldehydes in small amounts as well as the expected rearrangement products. A detailed study of the reaction mechanism revealed that the conversion occurs via an oxidative process through the consecutive formation of cycloheptadienes, cycloheptatrienes, and 1,1'-biphenyls. The acid-catalyzed rearrangement of 6-phenylbicyclo[3.2.0]hept-2-en-6-ols gave 1- and 2-phenylcycloheptatrienes directly, from which 1,1'-biphenyl and 1,1'-biphenyl-carbaldehydes were obtained by oxidation.

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