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[2.2]Paracyclophanes, structure and dynamics

Conference paper
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 48)

Abstract

Non-planar benzene rings, anomalous bond lengths and angles, and electronic interactions between parallel benzene nuclei are common features of the [2.2]paracyclophane system. This progress report reviews the unusual physical and, in particular, spectroscopic properties of such a strained molecular structure. Chirally substituted [2.2]paracyclophanes offer parallels to the stereochemistry of the metallocenes. Characteristics of the chemical behaviour of [2.2]paracyclophanes and analogous compounds comprise: transannular directing effects in electrophilic substitution, neighboring-group effects of the [2.2]paracyclophanyl moiety, cis-addition at the aliphatic bridges, dynamic intramolecular processes such as isomerization and racemization, and photochemical reactions.

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© Springer-Verlag 1974

Authors and Affiliations

  1. 1.Institut für organische Chemie der UniversitätWürzburg

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