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8685714 
Journal Article 
The Synthesis of Spiro[cyclohexane-1,9′-fluorene] and Related Compounds 
Baldwin, S; Baldwin, S 
1961 
Yes 
Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904 
26 
9 
3280-3287 
English 
The synthesis of the title compound (VI) is described (Chart I). A more direct route to the key intermediate spiro [cyclohexane-1,9′-fluoren]-4-one (V) is provided by the cyclization of 9,9-fluorenedipropionitrile (II) to 3-cyano-4-aminospiro-[Δ3-cvclohexene-1,9′-fluorene] (VII) by a catalytic quantity of potassium t-butoxide in t-butyl alcohol followed by hydrolysis to the spiro ketone V in an acetic-phosphoric acid mixture. Infrared and ultraviolet spectral evidence is presented for the entirely enolie structures of 3-carbomethoxyspiro [cyclohexane-l,9′-fluoren]-4-one (IVa) and 3-carboxamidospiro-[cyclohexane-1,9′-fluoren]-4-one (VIII), respectively. The structure and spectra of the interesting diketo spirane, 11,12-dihydro-1H,10H-benzo[h,i]fluoranthene-3,10-(2H)-dione (XI), are also discussed. 1961, American Chemical Society. All rights reserved.