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Proceedings of the National Academy of Sciences of the United States of America logoLink to Proceedings of the National Academy of Sciences of the United States of America
. 1981 Nov;78(11):6564–6566. doi: 10.1073/pnas.78.11.6564

Gas-phase pyrolytic formation and dimerization of benzocyclobutenes: Synthesis of [24](1,2,4,5) cyclophane

Bruce E Eaton 1, E D Laganis 1, V Boekelheide 1,*
PMCID: PMC349087  PMID: 16593108

Abstract

Gas-phase pyrolysis of benzocyclobutenes in a nitrogen stream at 450°C is a convenient efficient method for preparing dibenzocyclooctadienes. Application of this method to benzo[1,2;4,5]dicyclobutene gives [24](1,2,4,5)cyclophane directly. However, under the same reaction conditions, 3,6-dimethylbenzo[1,2;4,5]dicyclobutene gives the open [2.2]orthocyclophane derivative, whose structure has been established by x-ray crystallographic analysis of the corresponding iron complex.

Keywords: Flash pyrolysis, o-xylylenes, multibridged cyclophanes

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Laganis E. D., Finke R. G., Boekelheide V. Multilayered iron complexes of [2.2]paracyclophane. Proc Natl Acad Sci U S A. 1981 May;78(5):2657–2658. doi: 10.1073/pnas.78.5.2657. [DOI] [PMC free article] [PubMed] [Google Scholar]

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