The synthesis and some physical properties of several derivatives of cyclohept[e]indene have been described. The α,β-unsaturated ketone 1:2:3:5:6:7:8:9:10:5a:10a:10b-dodecahydrocyclohept[e]indene-5-one has been prepared. This compound was reduced initially with lithium aluminum hydride to 1:2:3:5:6:7:8:9:10:5a:10a:10b-dodecahydrocyclohept[e]indene-5-ol, which was subsequently further reduced catalytically to 1:2:3:4:5:6:7:8:9:10:3a:5a:10a:10b-tetradecahydrocyclohept[e]indene-5-ol. The ketone has also been reduced with hydrozine and base to the olefin 1:2:3:5:6:7:8:9:10:5a:10a:10b-dodecahydrocyclohept[e]indene. The latter compound has been subjected to various dehydrogenation conditions including reaction with sulfuric, selenium dichloro-dicyanoquinone and N-bromosuccinamide, as well as with heated contact catalysts including palladium on carbon and molybdenum, nickel sulfide in an effort to synthesize the non-benzenoid aromatic cyclohept[e]indene. None of the reactions has been completely successful, though dehydrogenation did occur to some extent. The partially aromatized compound 1:2:3:6:7:8:9:10-octahydrocyclohept[e]indene has been recovered and characterized, and spectral evidence suggests that 3:6:7:8:9:10-hexahydrocyclohept[e]indene has also been produced. Attempts to carry the dehydrogenation reactions beyond the oxidation state of the latter compound have been attempted but in no case has there been any indication of the non-benzenoid aromatic being formed. In most cases starting material was recovered or black polymeric products formed. The non-tendency of derivatives of cyclohept[e]indene to undergo elimination reactions that would lead to the fully conjugated system is, at present, in conflict with theoretically predicted stability for the system.