Journal of the American Chemical Society

Extreme Projection of a Proton into the π-Cloud of an Aromatic Ring: Record Shielding of an Aromatic Proton in trans-10 b-Methyl-10 c-(1-naphthyl)-10 b, 10 c- …

Y Ting, YH Lai

Index: Ting, Yuhua; Lai, Yee-Hing Journal of the American Chemical Society, 2004 , vol. 126, # 3 p. 909 - 914

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Citation Number: 17

Abstract

A synthetic sequence involving dithiametacyclophane→ metacyclophanediene→ dihydropyrene was employed to prepare trans-10 b-methyl-10 c-(2-naphthyl)-and trans-10 b- methyl-10 c-(1-naphthyl)-10 b, 10 c-dihydropyrene 5 and 6, respectively. Both exhibit a strong diamagnetic ring current despite the introduction of an internal bulky substituent within the π-electron cloud. Their electronic spectra suggest interaction between the two ...

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