Highly brominated biphenylenes as precursors for the convenient synthesis of 5,6,8,10-tetrabromobenzocyclooctene

Author:

Tutar Ahmet1,Cakmak Osman1,Karakas Mehmet1,Onal Adem1,Ide Semra12

Affiliation:

1. Department of Chemistry, Faculty of Science, Gaziosmanpasa University, 60240 Tokat, Turkey

2. Department of Physics Engineering, Hacettepe University, 06532 Beytepe, Ankara, Turkey

Abstract

An efficient synthesis is described of hexabromides 5 and 6 by photobromination of biphenylene (1). Double dehydrobromination of hexabromides 5 and 6 with t-BuOK affords 5,6,8,10-tetrabromobenzocyclooctene (7) in nearly quantitative yield. The tetrabromide 7 is a valuable precursor for the preparation of functionalised substituted benzocyclooctenes (benzo[8]annulenes).

Publisher

SAGE Publications

Subject

General Chemistry

Reference34 articles.

1. (a) CavaM.P., and MitchellM. J., Cyclobutadiene and Related Compounds, Academic Press, New York and London, 1965, p. 255.

2. BartonJ.W., in Nonbenzenoid Aromatics, ed SnyderJ.P., Academic Press, New York and London, 1969, p. 32.

3. Bromination of Methoxybiphenylenes

4. ShepherdM.K., Cyclobutarenes, Studies in Organic Chemistry No 44, Elsevier, 1991, pp. 157, 183, 208.

5. Four-membered ring compounds containing bis(methylene)cyclobutene or tetrakis(methylene)cyclobutane moieties. Benzocyclobutadiene, benzodicyclobutadiene, biphenylene, and related compounds

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