The irradiation (λ =403 nm) of α‐diazo‐2‐ethynylacetophenone (1 a) in solid argon at 10 K leads to (2‐ethynylphenyl)ketene (11) as the major product. A minor product is benzo‐4‐oxo‐2,5‐cyclohexadienylidene (6) which on 475‐nm irradiation reversibly rearranges to cycloprop[a]inden‐6(6aH)‐one (5a). This demonstrates that the intramolecular addition of the carbene center to the double bond can compete with the Wolff rearrangement.
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Komnick et al. (1996) studied this question.
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