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II.—The Attempted Synthesis of Benzo[a]biphenylene

Published online by Cambridge University Press:  14 February 2012

Neil Campbell  and
Robert A. N. Morris
Neil Campbell
Affiliation:
Department of Chemistry, University of Edinburgh.*
Robert A. N. Morris
Affiliation:
Department of Chemistry, University of Edinburgh.*
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Summary

Unsuccessful efforts to synthesize benzo[a]biphenylene and dibenzo-biphenylenes by the dehydrohalogenation of suitable intermediates are described. 2-o-Chlorophenyl-2-phenylpropionitrile with potassamide in liquid ammonia failed to give 8-cyano-7-phenylbicyclo[4,2,o]octa-I,3,5-triene, while diethyl 2-bromobenzylphenylmalonate with sodium in dry ethanol yielded I-phenylisochroman-3-one after hydrolysis. Bromination of 3,3′,4,4′-tetrahydro-2,2′-binaphthyl was accompanied by spontaneous dehydrobromination to yield 2,2′-binaphthyl, and interaction of phenyl-o-chlorophenylbromomethane with phenyllithium followed by chloracetic acid gave 1,2-di-o-chlorophenylethane.

Type
Research Article
Information
Proceedings of the Royal Society of Edinburgh Section A: Mathematics , Volume 68 , Issue 1 , 1968 , pp. 23 - 29
Copyright
Copyright © Royal Society of Edinburgh 1968

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