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[2.2] Paracyclophanes, structure and dynamics

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Stereochemistry II

Part of the book series: Topics in Current Chemistry Fortschritte der Chemischen Forschung ((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.

Chemistry of Phanes, Comm. 5. — Comm. 4 : Vögtle, F., Neumann, P.: Synthesis 1973, 85.

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    Prof. Dr. Fritz Vögtle & Dr. Peter Neumann

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Vögtle, F., Neumann, P. (1974). [2.2] Paracyclophanes, structure and dynamics. In: Stereochemistry II. Topics in Current Chemistry Fortschritte der Chemischen Forschung, vol 48. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-06682-9_48

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