1,3-Diphenylbenz[ƒ]inden-2-one (5) reversibly generated by thermal dissociation of its (π4 +π4)-dimer (4) adds stereospecifically to cis- and trans-but-2-ene; the related adducts (6) and (7) undergo smooth photodecarbonylation to the long-lived 2,3-naphthoquinodimethanes (2; R1= R2= Me) and (2; R1, R2=[CH2]4).
D. W. Jones, A. Pomfret and R. L. Wife, J. Chem. Soc., Chem. Commun., 1980, 463 DOI: 10.1039/C39800000463
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