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Styrylcyclohex-2-enones (3a-d) are cyclized photochemically to 2,3-dihydro-1H-phenanthren- 4-ones (4a-d). The corresponding phenanthren-4-ones with a methoxy group at C-5 (opposing the carbonyl at C-4) are not formed. The starting material 3a was prepared employing a Heck reaction of the styrenes 1a with 5,5- dimethyl-3-chlorocyclohex-2-enone (2a) and 5,5-dimethyl-3-bromocyclohex-2-enone (2b) (Scheme 1). Since both of the halides afforded the dienone 3a in good yield, the more easily available chloro compound 2a was used in the subsequent preparation of 3b-e starting from the styrenes 1b-e. The crystalline dienones had the E configuration as deduced from the coupling

Photocyclization of 3-styrylcyclohex-2-enones to 2,3-dihydro-1H-phenanthren-4-ones