Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Layered Compounds. XVI. NMR Spectra of Multilayered [2.2]Paracyclophanes
Tetsuo OtsuboShigeyoshi MizogamiYoshiteru SakataSoichi Misumi
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1973 Volume 46 Issue 12 Pages 3831-3835

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Abstract

The NMR spectra of multilayered [2.2]paracyclophanes (I–XVI), in which benzene rings are closely stacked, have been examined. The assignment of the signals was made not only by integral strength, but also by solvent effect and the Nuclear Overhauser effect. The steric compression effect of transannular methyl groups on aromatic protons was observed in methylated cyclophanes. Enhanced ortho substitution shift was also observed. All the aromatic protons shift to remarkably higher field due to the anisotropy of stacked benzene rings as the number of layers increases. The shielding effect caused by these rings was empirically estimated.

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