Products of reaction of 1-phenyltricyclo[4.1.0.02,7]heptane with N-iodosuccinimide in aqueous THF

Abstract

Iodohydroxylation of 1-phenyltricyclo[4.1.0.0^2,7]heptane in aqueous THF at 20°C with N-iodosuccinimide proceeds at the central bicyclobutane bond C¹–C⁷ and results in the formation of two-component mixture of diastereomeric 7-iodo-6-phenyl-6-norpinanols in the ratio 1 : 1.8 in favor of the product of the anti-addition. Treating of iodonorpinanols with trimethylamine in aqueous THF affords 1-benzoylcyclohex-1-ene as a result of 1,4-dehydroiodination accompanied with the Grob fragmentation of the carbon scaffold.