The highly strained and distorted ketone 1,2,3-trihydrocyclohepta[3,4,5,6-def]biphenylene-2-one 5 is prepared in 17% yield by cyclization of 1 with TsCNMe (Ts = p-Me-C6H4SO2); the X-ray analysis of 5 exhibits an extremely elongated C(4a)–C(4b) bond (156.4 pm) and a strong alternation of bond lengths in both benzene rings.
F. Vögtle, J. E. Schulz and K. Rissanen, J. Chem. Soc., Chem. Commun., 1992, 120 DOI: 10.1039/C39920000120
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