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Cyclopropene formed the exo and endo Diels–Alder adducts in a 1 : 1 ratio with furan; only the endo-isomer readily rearranges to cycloheptadienones.

The reactivity sequence tetralin-1-ol > indan-1-ol tetrahydrobenzocyclohepten-1-ol is observed in the dehydrogenation of these benzyl alcohols to the corresponding ketones by dichlorodicyanobenzoquinone. There is a linear relationship between the angle of inclination of the tertiary benzylic C–H bond to the plane of the aromatic ring and log k, reflecting the degree of σ–π overlap in the transition state for the oxidation. Factors underlying the preferred pseudo-axial conformation of the benzylic hydroxy-groups in these benzocycloalkenols are discussed.

In the Type II photochemical reactions of cis-2-propyl-4-t-butylcyclohexanone, the ratio of cyclobutanols to fragmentation products is 13 : 87 for the singlet-state reaction and 68 : 32 for the triplet-state reaction, showing that, in the latter state at least, there is a noticeable stereoelectronic effect on the fragmentation reaction.