Flash pyrolysis of vinylidencyclopentadiene at 800–1050°C results in carbon randomization; 2-methyl-vinylidenecyclopentadiene rearranges to styrene and benzocyclobutene, and [1-13C]phenyldiazomethane yields vinylidenecyclopentadiene carrying excess label at C(5) at 590°C and 5–7 mmHg of N2, thus suggesting that the ring contraction is reversible and occurs via bicyclo-[3.2.0]hepta-1,3,6-triene.
C. Wentrup, E. Wentrup-Byrne and P. Müller, J. Chem. Soc., Chem. Commun., 1977, 210 DOI: 10.1039/C39770000210
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