Hostname: page-component-745bb68f8f-d8cs5 Total loading time: 0 Render date: 2025-01-12T23:47:50.642Z Has data issue: false hasContentIssue false
  • English
  • Français

22.—Attempted Synthesis of Dibenzo[a,g]biphenylene.*

Published online by Cambridge University Press:  14 February 2012

Neil Campbell ,
R. S. Macpherson  and
R. A. N. Morris
Neil Campbell
Affiliation:
Department of Chemistry, University of Edinburgh
R. S. Macpherson
Affiliation:
Department of Chemistry, University of Edinburgh
R. A. N. Morris
Affiliation:
Department of Chemistry, University of Edinburgh
Get access Rights & Permissions [Opens in a new window]

Abstract

α-Truxillic acid (1, R = CO2H) (Criegee and Höver 1960) underwent the Arndt-Eistert reaction to yield l,3-diphenylcyclobutane-2,4-diacetic acid (1, R = CH2·CO2H), cyclisation of which with hydrogen fluoride gave cis-trans-cis-5,6,6a,6b, 11,12,12a, 12b-octahydro-5,11-dioxodibenzo[a,g]biphenylene (11). Attempts to aromatise the compound by bromination with N-bromosuccinimide followed by treatment with pyridine or potassium acetate were unsuccessful. The ketone was therefore reduced with potassium borohydride to the corresponding diol (11, CO replaced by CHOH) in the hope that dehydration of the product followed by mild dehydrogenation would yield dibenzo[a,g]biphenylene, but the only product isolated was naphthalene.

Type
Research Article
Information
Proceedings of the Royal Society of Edinburgh Section A: Mathematics , Volume 71 , Issue 4 , 1974 , pp. 275 - 277
Copyright
Copyright © Royal Society of Edinburgh 1974

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

References to Literature

Bryce-Smith, D. and Vickery, B., 1961. Chemy Ind., 429.Google Scholar
Caglioti, L., 1966. Tetrahedron, 22, 487.Google Scholar
Criegee, R. and Hover, H., 1960. Chem. Ber., 93, 2521.Google Scholar
Lemieux, R. and Johnson, W. S., 1956. J. Org. Chem., 21, 478.Google Scholar
Witing, G., Koenig, G. and Claus, K., 1955. Justus Liebigs Annln Chem., 593, 27.Google Scholar