Phenylcarbene and tropylidene interconvert in the gas‐phase, as evidenced by the formation of stilbene and heptafulvalene ( 5 ) from both at 300°. Heptafulvalene itself rearranges to stilbene and anthracene above 500°. Phenylcarbene, but not tropylidene, undergoes ring contraction to fulvenallene ( 9 ) at 900°. Formation of fluorene from diphenylcarbene involves a complete ring expansion to 2‐phenyltropylidene ( 14 ), and subsequent ring contraction to 2‐biphenylylcarbene ( 15 ).
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Wentrup et al. (1970) studied this question.
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