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The Radical Cations of 4,5,7,13,15,16-Hexamethyl- and 4,5,7,8,12,13,15,16-Octamethyl [2.2]paracyclophane

✍ Scribed by Fabian Gerson; Javier Lopez; Henning Hopf

Publisher: John Wiley and Sons
Year: 1982
Tongue: German
Weight: 307 KB
Volume: 65
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19820650511

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✦ Synopsis

Abstract

4,5,7,13,15,16‐Hexamethyl‐ (3) and 4,5,7,8,12,13,15,16‐octamethyl[2.2]paracyclophane (4) have been oxidized to their radical cations in solution under relatively mild conditions. Substantial hyperfine splittings in the ESR. spectra of 3⊕. and 4⊕. arise from the methyl protons, whereas those from methylene protons are very small. This result indicates that the ethano bridges, unlike the methyl substituents, are rather ineffective in delocalizing the positive charge in 3⊕. and 4⊕. It is in line with the interpretation proposed previously to rationalize the gas‐phase ionization potentials of multiply bridged [2~N~]cyclophanes and methyl derivatives of [2.2]paracyclophane. The π‐spin distributions in 3⊕. and 4⊕. are discussed in terms of a simple model in which the singly occupied orbitals are represented as the antibonding combinations of two benzene HOMO's.

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