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VIII.—Some 9-Fluorenyl and 9,9′-Bifluorenyl Derivatives.*

Published online by Cambridge University Press:  14 February 2012

J. M. Birnie  and
Neil Campbell
J. M. Birnie
Affiliation:
Department of Chemistry, University of Edinburgh.
Neil Campbell
Affiliation:
Department of Chemistry, University of Edinburgh.
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Summary

9-Carbamoylfluorene with lithium aluminium hydride, 9-cyanofluorene with this reagent and aluminium trichloride, or (on one occasion) treatment of the oximes of 9-formylfluorene with thionyl chloride yield 9,9′-dicyano-9,9′-bifluorenyl. 9-Bromofluorene and ethanolic potassium cyanide yield 9-cyano-9,9′-bifluorenyl, and 9-formylfluorene when kept in ether for a month gives 9,9′-diformyl-9,9′-bifluorenyl. The so-called α-oxime of 9-formylfluorene described in the literature contains about 33 per cent of the higher melting β-oxime. Reduction of the oximes with zinc and acetic acid yields di(9-fluorenylidenemethyl)amine, previously obtained by other methods. A new method for the preparation of 9-aminomethylenefluorene is described and its structure has been confirmed. Many 9-substituted and 9,9′-disubstituted fluorenes exhibit characteristic absorption at 1920–1880 and 1960–1940 cm.−1.

Type
Research Article
Information
Proceedings of the Royal Society of Edinburgh Section A: Mathematics , Volume 68 , Issue 2 , 1969 , pp. 120 - 126
Copyright
Copyright © Royal Society of Edinburgh 1969

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References

References to Literature

Bellamy, L. J., 1958. The Infrared Spectra of Complex Molecules, p. 90. London: Methuen.Google Scholar
Bethell, D., Cockerill, A. F., and Frankham, D. F., 1967. J. Chem. Soc., B, 1287.Google Scholar
Campbell, N., Craig, J. T., and Delahunt, K. W., 1967. Chemy Ind., 1361.Google Scholar
Cavalla, J. F., Simpson, R., and White, A. C., 1967. Chemy Ind., 1961.Google Scholar
Greenhow, E. J., Harris, A. S., and White, F. N., 1954. J. Chem. Soc., 3116.Google Scholar
Humber, L. H., and Davies, M. A., 1966. Can. J. Chem., 44, 2133.CrossRefGoogle Scholar
Karabatsos, G. J., and Taller, R. A., 1968. Tetrahedron, 24, 3347.CrossRefGoogle Scholar
Koelsch, C. F., 1961. J. Org. Chem., 26, 1291.Google Scholar
Miller, F. D., and Wagner, E. C., 1951. J. Org. Chem., 16, 279.Google Scholar
Pejkovic-Tadic, I.et al., 1965. Helv. Chim. Acta, 48, 1157.CrossRefGoogle Scholar
Stolle, R., Munzel, H., and Wolf, F., 1913. Ber. Dt. Chem. Ges., 46, 2343.Google Scholar
Von, I., and Wagner, E. C., 1944. J. Org. Chem., 9, 155.Google Scholar
Wislicenus, W., and Russ, K., 1910. Ber. Dt. Chem. Ges., 43, 2719.CrossRefGoogle Scholar