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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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