1,3-Cyclohexadiene → 3-(3,4-Dichlorophenyl)bicyclo[2.2.2]oct-5-ene-2-carbonitrile

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Reaction Steps

trans-3,4-Dichlorocinnamonitrile (20 g.) and cyclohexadiene (16 g.) were heated at 150°C. for 3 weeks. The solution was evaporated, the resultant oil purified by column chromatography and crystallised from methanol to yield white crystals of 5-cyano-6-(3',4'-dichlorophenyl)bicyclo[2,2,2]oct-2-ene. The latter (14 g.) was hydrogenated as described in Example 1 to yield trans-3-cyano-2-(3',4'-dichlorophenyl)bicyclo[2,2,2]octane as white crystals (14 g.). Similarly the following compounds were prepared:

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